[ CAS No. 85475-01-0 ] {[proInfo.proName]}

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Quality Control of [ 85475-01-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 85475-01-0 ]

SDS Specification

Alternatived Products of [ 85475-01-0 ]

Product Details of [ 85475-01-0 ]

CAS No. :	85475-01-0	MDL No. :	MFCD12783671
Formula :	C₅H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	119.16	Pubchem ID :	-
Synonyms :		Chemical Name :	2-(2-(Methylamino)ethoxy)ethanol

Safety of [ 85475-01-0 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P210-P260-P264-P270-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	2735
Hazard Statements:	H302-H335-H314-H227	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 85475-01-0 ]

* 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.

Upstream synthesis route of [ 85475-01-0 ]
Downstream synthetic route of [ 85475-01-0 ]

[ 85475-01-0 ] Synthesis Path-Upstream 1~1

1
[ 67-56-1 ]
[ 929-06-6 ]
[ 110-91-8 ]
[ 1704-62-7 ]
[ 85475-01-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2002, vol. 41, # 18, p. 3476 - 3479

[ 85475-01-0 ] Synthesis Path-Downstream 1~4

1
[ 593-51-1 ]
[ 118591-58-5 ]
[ 85475-01-0 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate; In 1,4-dioxane; at 50℃;	Compound 1-3 (5.1 g, 19.6 mmol) was dissolved in 1,4-dioxane (50 mL), followed by addition of methylamine hydrochloride 1-4 (13.4 g, 196 mmol), and potassium carbonate (13.8 g, 100 mmol) was added under stirring in batches, followed by stirring the reaction overnight under conditions of 50° C. and a closed reaction system, TLC monitoring showed that the starting material 1-3 was completely reacted. The solvent was removed under reduced pressure to obtain a concentrated residue. The concentrated residue was dispensed with dichloromethane (20 mL), an appropriate amount of silica gel was added and the sample was stirred, spin-dried under reduced pressure and directly placed on a silica gel column for column chromatographic purification, with an eluent (dichloromethane:methanol=20/1-5/1) to obtain the target product 1-5 (1.2 g, 52percent) as a pale yellow oil, LC-MS: m/z=120[M+H]+.

Reference： [1]Patent: US2017/2028,2017,A1 .Location in patent: Paragraph 0090; 0092

2
[ 85475-01-0 ]
[ 436857-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / 0 °C 2: triethylamine / dichloromethane 3: sodium azide / N,N-dimethyl-formamide / 70 °C 4: palladium 10% on activated carbon; hydrogen
	Multi-step reaction with 4 steps 1: triethylamine 2: triethylamine / dichloromethane 3: sodium azide / N,N-dimethyl-formamide / 70 °C 4: palladium 10% on activated carbon; hydrogen
	Multi-step reaction with 3 steps 1: triethylamine 2: triethylamine / dichloromethane 3: sodium azide / N,N-dimethyl-formamide / 70 °C

Reference： [1]Current Patent Assignee: ARRAKIS THERAPEUTICS INC - WO2017/136450, 2017, A2
[2]Current Patent Assignee: ARRAKIS THERAPEUTICS INC - WO2018/6074, 2018, A2
[3]Current Patent Assignee: ARRAKIS THERAPEUTICS INC - WO2019/109046, 2019, A1

3
[ 118591-58-5 ]
[ 74-89-5 ]
[ 85475-01-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	at 85℃; for 16h;Inert atmosphere;	A mixture of 2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate (3 g, 11.52 mmol, 1 eq) in methanamine (11.93 g, 115.25 mmol, 10 eq) was degassed and purged with nitrogen for 3 times, and then the mixture was stirred at 85 C for 16 hours under nitrogen. The reaction mixture was concentrated under reduced pressure to give a residue. Compound 2-[2- (methylamino)ethoxy] ethanol (1.37 g, 11.50 mmol, 99% yield) was obtained as a yellow oil. 'H- NMR (400MHz, CDCb) d 3.72 - 3.47 (m, 8H), 2.67 - 2.63 (m, 3H).
	at 70℃; for 12h;Sealed tube;	A solution of 2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate (2.50 g, 9.60 mmol, 1 eq) and methanamine (40.0 mL, 1.00 eq) in sealed tube was stirred at 70 C. for 12 hours. Analysis by TLC indicated 2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate was consumed completely. The reaction mixture was concentrated under reduced pressure to remove methanamine (40.0 mL, 1.00 eq) to give 2-[2-(methylamino)ethoxy]ethanol (1.10 g, crude) as a yellow oil.

Reference： [1]Patent: WO2019/195609,2019,A2 .Location in patent: Paragraph 00707-00708
[2]Patent: US2019/151295,2019,A1 .Location in patent: Paragraph 1476-1477

4
[ 85475-01-0 ]
[ 951207-88-8 ]
N-[2-(2-hydroxyethoxy)ethyl]-2-(1H-indole-3-carbonyl)-N-methyl-thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 12h;	1.1 Step 1 : [2-(2-Hydroxyethoxy)ethyl]-2-(1H-indole-3-carbonyl)-methyl-thiazole-4- carboxamide To a stirred solution of 2-(lT/-indole-3-carbonyl)thiazole-4-carboxylic acid (100 mg, 348.91 pmol, 1 eq) and 2-[2-(methylamino)ethoxy]ethanol (50 mg, 419.60 pmol, 52.40 pL, 1.2 eq) in DMF (5 mL) was added HATU (199.00 mg, 523.36 pmol, 1.5 eq) and DIEA (90.19 mg, 697.81 pmol, 121.54 pL, 2 eq). The reaction mixture was stirred at 25 °C for 12 h. The reaction mixture was filtered and the filtrate was purified by preparative HPLC (column: Agela DuraShell C18 15025mm5um; mobile phase: [water (0.04%NH3H20+10mM NH4HC03)-ACN]; B%: 27%-57%, lOmin). The desired fraction was lyophilized to yield A-[2-(2-hydroxyethoxy)ethyl]-2- (lT -indole-S-carbony^-jV-methyl-thiazoleM-carboxamide (29.96 mg, 80.23 pmol, 23.0% yield, 100.0% purity) as white solid. NMR (400 MHz, DMSO -d6) ppm 8.95 (s, 1H), 8.42-8.38 (m, 1H), 8.33 (d, J= 8.5 Hz, 1H), 7.57 (d, J= 5.8 Hz, 1H), 7.32-7.26 (m, 2H), 3.78-3.67 (m, 4H), 3.49 (d, J= 16.3 Hz, 4H), 3.18 (s, 3H); ES-LCMS m/z 374.0 [M+H]+.

Reference： [1]Current Patent Assignee: IKENA ONCOLOGY INC - WO2021/127302, 2021, A1 Location in patent: Paragraph 00162; 00185

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[ CAS No. 85475-01-0 ] {[proInfo.proName]}

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[ 85475-01-0 ] Synthesis Path-Upstream 1~1

[ 85475-01-0 ] Synthesis Path-Downstream 1~4

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