[ CAS No. 89364-41-0 ] {[proInfo.proName]}

Name: 89364-41-0|1,4-Dioxane-2-carboxylic acid|95%
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SKU: A802384
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Quality Control of [ 89364-41-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89364-41-0 ]

CAS No. :	89364-41-0	MDL No. :	MFCD06260725
Formula :	C₅H₈O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VGBAYGFELCUXBS-UHFFFAOYSA-N
M.W :	132.11	Pubchem ID :	5230755
Synonyms :

Calculated chemistry of [ 89364-41-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	27.98
TPSA :	55.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.02
Log Po/w (XLOGP3) :	-0.67
Log Po/w (WLOGP) :	-0.51
Log Po/w (MLOGP) :	-1.23
Log Po/w (SILICOS-IT) :	0.27
Consensus Log Po/w :	-0.22

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-0.17
Solubility :	89.1 mg/ml ; 0.675 mol/l
Class :	Very soluble
Log S (Ali) :	-0.03
Solubility :	124.0 mg/ml ; 0.94 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.42
Solubility :	349.0 mg/ml ; 2.64 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.71

Safety of [ 89364-41-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89364-41-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 89364-41-0 ]

[ 89364-41-0 ] Synthesis Path-Downstream 1~25

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

2
[ 89364-41-0 ]
[ 1372187-09-1 ]
(6R,7R)-tert-butyl 6-((1,4-dioxane-2-carboxamido)methyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 20℃; for 3h;	37 5.1.23 (6R,7R)-tert-Butyl 7-(4-chloro-3-fluorophenyl)-6-((3-methoxypropanamido)methyl)-1,4-oxazepane-4-carboxylate General procedure: To a mixture of 26b (100 mg, 0.28 mmol), 3-methoxypropionic acid (31.4 μL, 0.33 mmol), HOBt·H2O (45.2 mg, 0.33 mmol) and Et3N (97 μL, 0.70 mmol) in THF (1.4 mL) was added WSC·HCl (64.1 mg, 0.33 mmol). The mixture was stirred at room temperature for 3 h, and then poured into water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, Hexane/EtOAc) to give (6R,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-methoxypropanamido)methyl)-1,4-oxazepane-4-carboxylate (81 mg, 65%) as a colorless oil.

Reference： [1]Yukawa, Tomoya; Fujimori, Ikuo; Kamei, Taku; Nakada, Yoshihisa; Sakauchi, Nobuki; Yamada, Masami; Ohba, Yusuke; Ueno, Hiroyuki; Takiguchi, Maiko; Kuno, Masako; Kamo, Izumi; Nakagawa, Hideyuki; Fujioka, Yasushi; Igari, Tomoko; Ishichi, Yuji; Tsukamoto, Tetsuya [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 14, p. 3207 - 32174]

3
[ 89364-41-0 ]
[ 6610-29-3 ]
5-(1,4-dioxan-2-yl)-4-methyl-4H-1,2,4-triazole-3-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.21%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃; Cooling with ice;	10 Preparation 10: 5 -(1 ,4-dioxan-2-yl)-4-methyl-4H- 1 ,2,4-triazole-3 -thiol To a solution of 1,4-dioxane-2-carboxylic acid (0.5 g, 3.78 mmol) in DMF (2.23 mL),4-Methyl-3-thiosemicarbazide (0.44 g, 26.55 mmol) was added. DIPEA (1.16 mL, 6.8 mmol)was added dropwise at RT, then the mixture was cooled in an icebath before adding T3P (50%w/w in EtOAc) (3.37 mL, 5.67 mmol). The reaction was stirred at RT ON. NaOH 4 M solution was added (resulting pH=8). The reaction was diluited with EtOAc and the two resulting phases were separated. The pH of the aqueous layer was increased to 11 NaOH 4 M and the mixtureheated to 70°C for 40 mm. The solution was cooled to RT, then cooled down to 0 °C and HC1 6N was slowly added till pH5. The aqueous layer was extracted three times with DCM andcombined organics were dried and concentrate under vacuum. The crude was purified by FC on Si02 (eluent: from cyclohexane to 50% of ethyl acetate) to give 0.489 g of title compound aswhite solid (plO, yield 64.2 1%). MS (m/z): 202.0 [IVII{]t

Reference： [1]Current Patent Assignee: INDIVIOR PLC - WO2017/21920, 2017, A1 Location in patent: Paragraph 0514; 0515

4
[ 89364-41-0 ]
3-[(3-chloropropyl)sulfanyl]-5-(1 ,4-dioxan-2-yl)-4-methyl-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide; ethyl acetate / 20 °C / Cooling with ice 2: potassium carbonate / methanol; acetone / 4 h / 20 °C

Reference： [1]Current Patent Assignee: INDIVIOR PLC - WO2017/21920, 2017, A1

5
[ 89364-41-0 ]
6-chloro-4-(2,4-difluorophenyl)picolinonitrile [ No CAS ]
[ 76-05-1 ]
4-(2,4-difluorophenyl)-6-(1,4-dioxan-2-yl)picolinonitrile trifluoroacetate [ No CAS ]
4-(2,4-difluorophenyl)-5-(1,4-dioxan-2-yl)picolinonitrile trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.8 mg	Stage #1: 1,4-dioxane-2-carboxylic acid; 6-chloro-4-(2,4-difluorophenyl)picolinonitrile With (1,2-dimethoxyethane)dichloronickel(II); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Glovebox; UV-irradiation; Stage #2: trifluoroacetic acid In water; acetonitrile

Reference： [1]Zhang, Rui; Li, Guoqing; Wismer, Michael; Vachal, Petr; Colletti, Steven L.; Shi, Zhi-Cai [ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 773 - 777]

6
[ 89364-41-0 ]
[ 1121057-75-7 ]
1,4-dioxane-2-yl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl]methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.3 g		1,2,3,6-tetrahydro pyridin-4-yl-boron acid Triethylamine (2.84 mL) is added to the N.N-dimethylformamide (20 mL) solution of pinacol ester salt acid chloride (CAS number: 1121057-75-7) (2.50 g), It stirred for 5 minutes at the room temperature. 4-(4,6-dimethoxy- 1,3,5-triazine 2-yl)-4-methylmorpholinium Chloride (4.20 g) and 1,4-dioxane 2-carboxylic acid (1.61 g) was added, and it stirred at the room temperature for 18 hours. Water was added to reaction mixture, the organic layer was washed twice with water after extraction with ethyl acetate, and the saturated sodium chloride solution washed further. After drying with anhydrous sodium sulfate, the mark compound (2.30 g) was obtained as a brown oily matter by condensing under decompression.

Reference： [1]Patent: JP2016/128387,2016,A .Location in patent: Paragraph 0322

7
[ 89364-41-0 ]
1-(5-{3-[1-(1,4-dioxane-2-ylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-5-methylphenoxy}-4-methyl-2,3-dihydro-1H-indole-1-yl)-2-[2-(methylsulfonyl)phenyl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 18 h / 20 °C 2.1: sodium carbonate / 1,2-dimethoxyethane; water / 0.08 h / 20 °C 2.2: 0.5 h / 130 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - JP2016/128387, 2016, A

8
[ 89364-41-0 ]
1-(5-{3-[1-(1,4-dioxane-2-ylcarbonyl)piperidine-4-yl]-5-methylphenoxy}-4-methyl-2,3-dihydro-1H-indole-1-yl)-2-[2-(methylsulfonyl)phenyl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 18 h / 20 °C 2.1: sodium carbonate / 1,2-dimethoxyethane; water / 0.08 h / 20 °C 2.2: 0.5 h / 130 °C / Microwave irradiation 3.1: palladium-carbon; hydrogen / ethyl acetate; tetrahydrofuran / 15 h / 20 °C

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - JP2016/128387, 2016, A

9
[ 89364-41-0 ]
1-{4-methyl-5-[3-methyl-5-(piperidine-3-yl)phenoxy]-2,3-dihydro-1H-indole-1-yl}-2-[2-(methylsulfonyl)phenyl]ethanone hydrochloride [ No CAS ]
1-(5-{3-[1-(1,4-dioxane-2-ylcarbonyl)piperidine-3-yl]-5-methylphenoxy}-4-methyl-2,3-dihydro-1H-indole-1-yl)-2-[2-(methylsulfonyl)phenyl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.6 mg	Stage #1: 1-{4-methyl-5-[3-methyl-5-(piperidine-3-yl)phenoxy]-2,3-dihydro-1H-indole-1-yl}-2-[2-(methylsulfonyl)phenyl]ethanone hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 1,4-dioxane-2-carboxylic acid With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In N,N-dimethyl-formamide at 20℃; for 18h;	35c Triethylamine (50 muL) was added to the N.N-dimethylformamide (3 mL) solution of the obtained compound (100 mg), and it stirred for 5 minutes at the room temperature. 4-(4,6-dimethoxy- 1,3,5-triazine 2-yl)-4-methylmorpholinium Chloride (74.8 mg) and 1,4-dioxane 2-carboxylic acid (28.6 mg) was added, and it stirred at the room temperature further for 20 hours. Water was added to reaction mixture and ethyl acetate extracted. Water and a saturated sodium chloride solution washed the organic layer, and after drying with anhydrous sodium sulfate, it condensed under decompression. By refining the obtained residue with silica gel column chromatography (ethyl acetate/dichloromethane), the mark compound (88.6 mg) was obtained as a white solid.

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - JP2016/128387, 2016, A Location in patent: Paragraph 0326; 0329

10
[ 89364-41-0 ]
[ 22945-22-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,4-dioxane-2-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 3 - 20℃; for 3.33333h; Cooling with ice; Stage #2: With ammonium hydroxide for 2h;	4P Example 4P1 ,4-dioxane-2-carboxamide In a 1 L recovery flask, 1 ,4-dioxane-2-carboxylic acid (11.0 g) in tetrahydrofuran (200 mL) was cooled to 3 °C, and di(1H- imidazol-1-yl)methanone (16 g) was added all at once. The mixture was stirred cold for 5 minutes, and stirred at room temperature for 2 hours. The mixture was then cooled inan ice-water bath for 15 minutes, concentrated ammonium hydroxide (16 mL) was added, and the reaction was stirred for 1 hour. The cold bath was removed and the reaction was stirred another 1 hour. The mixture was concentrated and left under high vacuum overnight. The material was taken up in 150 mL ethyl acetate and 40 mL 6N aqueous HC1. The layers were separated, and the aqueous layer was extracted with 4 x 200 mL ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude product was carried on without further purification.

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/35911, 2019, A1 Location in patent: Paragraph 00201

11
[ 89364-41-0 ]
methyl 1,4-dioxane-2-carbimidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 3.33 h / 3 - 20 °C / Cooling with ice 1.2: 2 h 2.1: dichloromethane / 0.25 h / Cooling with ice 2.2: 20 °C

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/35911, 2019, A1

12
[ 89364-41-0 ]
5-amino-6-((2,4-dimethoxybenzyl)amino)-N-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)benzyl)pyrimidine-4-carboxamide [ No CAS ]
C₂₉H₂₈FN₇O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92 mg	Stage #1: 1,4-dioxane-2-carboxylic acid; 5-amino-6-((2,4-dimethoxybenzyl)amino)-N-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)benzyl)pyrimidine-4-carboxamide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate at 150℃; for 4h; Microwave irradiation; Stage #2: With trifluoroacetic acid In ethyl acetate at 20℃; for 3h;	32.H H) 8-(1,4-dioxan-2-yl)-N-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)benzyl)-7H-purine-6-carboxamide A mixture of 5-amino-6-((2,4-dimethoxybenzyl)amino)-N-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)benzyl)pyrimidine-4-carboxamide (120 mg), 1,4-dioxane-2-carboxylic acid (81 mg), DIEA (0.213 mL), 1.7 M T3P/ ethyl acetate solution (0.431 mL) and THF (2.5 mL) was stirred under microwave irradiation at 150°C for 4 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give an oil (92 mg). A mixture of the obtained oil (92 mg), TFA (3 mL) and ethyl acetate (2 mL) was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (46.0 mg). 1H NMR (300 MHz, DMSO-d6) δ 3.60-3.82 (3H, m), 3.85 (3H, s), 3.87-4.03 (3H, m), 4.58 (2H, d, J = 6.2 Hz), 4.99 (1H, d, J = 7.3 Hz), 7.00 (1H, d, J = 9.2 Hz), 7.28-7.33 (1H, m), 7.42 (1H, s), 7.88 (1H, d, J = 0.8 Hz), 8.16 (1H, s), 9.01 (1H, brs), 9.83 (1H, brs), 13.43 (1H, s).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP3514149, 2019, A1 Location in patent: Paragraph 0292-0299

13
[ 89364-41-0 ]
[ 15957-23-0 ]