Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 763111-47-3 | MDL No. : | |
Formula : | C20H19FN4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MFFUYEOGICAKCK-UHFFFAOYSA-N |
M.W : | 366.39 | Pubchem ID : | 11726399 |
Synonyms : |
|
Chemical Name : | 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one |
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 107.8 |
TPSA : | 78.09 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.46 cm/s |
Log Po/w (iLOGP) : | 2.57 |
Log Po/w (XLOGP3) : | 1.52 |
Log Po/w (WLOGP) : | 1.36 |
Log Po/w (MLOGP) : | 2.7 |
Log Po/w (SILICOS-IT) : | 3.84 |
Consensus Log Po/w : | 2.4 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.24 |
Solubility : | 0.209 mg/ml ; 0.000571 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.77 |
Solubility : | 0.625 mg/ml ; 0.0017 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -6.83 |
Solubility : | 0.0000541 mg/ml ; 0.000000148 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride In ethanol; water at 20℃; for 3 h; | at room temperature 2A (13.6 g, 29 mmol) is dissolved into 30 ml in ethanol, adding 6 N hydrochloric acid solution of 60 ml and stirring 3 h. The reaction liquid concentrated to 50 ml, for 4 N of NH4 OH adjusting pH to 10. In order to DCM (3 × 50 ml) extraction mixed solution, organic phase to 50 ml water washing after adding anhydrous sodium sulfate drying and a half hours. Filtering to remove the sodium sulfate, the filtrate overnight after standing separate products, filtered to obtain the title compound (white solid, 9.9 g, yield 92percent). |
81% | With trifluoroacetic acid In dichloromethane at 10 - 30℃; for 3 h; Green chemistry; Large scale | General procedure: The compound of formula C (1.21 kg, 2.59 ml) was dissolved in dichloromethane (2.4 L) and stirred well. Trifluoroacetic acid (3.25 kg, 28.5 mo 1, the molar ratio of compound of formula C to trifluoroacetic acid Ratio of 1:11),Rose to 10 ° C ~ 30 ° C the reaction was stirred for 3h. Evaporation of methylene chloride and trifluoroacetic acid to the residue first added water (1.21L), filtered, the filtrate was taken, and then added n-hexane (1.21L) was extracted four times, the aqueous phase was taken, with ammonia to adjust PH to 8 ~ 10, stirring 1.5h, filtered, take the filter cake, dried to give Olaparib intermediate (Β) 0.78kg,Yield 82percent, purity 96.4percent). Only the extraction solvent in step (1) of Example 1 was replaced with butyl acetate, and the others were kept constant to afford the Olaparib intermediate (Β) (0.77 kg, yield 81percent, purity 99.8percent, impurity A' in an amount of 0.2percent). |
58.5% | Stage #1: With hydrogenchloride; water In industrial methylated spirits at 15 - 25℃; for 0.5 h; Stage #2: With ammonia; water In dichloromethane |
(b) 4-[4-Fluoro-3-(piperazine-1-carbonyl)-benzyl]-2H-phthalazin-1-one (B) To a stirred solution of industrial methylated spirits (IMS) (2200 ml) and concentrated HCI (4400 ml) was added compound C (2780.2 g) in portions at room temperature under nitrogen, the foaming was controlled by the addition rate. The solution was then stirred at 15 to 250C for 30 minutes and sampled for completion (HPLC).Upon completion the solution was evaporated to remove any IMS and the aqueous extracted with CH2CI2 (2 x 3500 ml) before the pH was adjusted to >8 using concentrated ammonia. The resultant slurry was then diluted with water (10000 ml) and extracted with CH2CI2 (4 x 3500 ml), washed with water (2 x 2000 ml), dried over MgSO4 (25Og) and evaporated. The crude product was then slurried in CH2CI2 (3500 ml) and added to MTBE (5000 ml). The resultant suspension was filtered and dried at 500C overnight yielding 611.O g (58.5percent yield) of material with a purity of 94.12percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.1% | With piperazine; sulfuric acid In acetonitrile at 78 - 80℃; | A solution of 1-5 - [(3,4-dihydro-4-oxo-l-phthalazinyl) methyl] -2- fluorobenzoic acid (60.0 g, 0.20 mol)Suspended in 600 mL of acetonitrile,Anhydrous piperazine (43.0 g, 0.50 mol)Piperazine dihydrochloride (79.0 g, 0.50 mol)Concentrated sulfuric acid (2.78 ml, 0.04 mol)Heated to 78-80 ° C under reflux for 7 to 8 hours,Drop to room temperature,Concentrated under reduced pressure acetonitrile, water was added 1000ml, stirred for 30min; concentrated ammonia was added dropwise to a PH value of 7-8, stirred 2h, suction filtration,44.1 g of 1- [5 - [(3,4-dihydro-4-oxo-1-phthalazinyl) methyl] -2-fluorobenzoyl] piperazine was obtained in a yield of 60.1percent.1- [5 - [(3,4-dihydro-4-oxo-1-phthalazin-yl) methyl] -2-fluorobenzoyl] piperazine 1H NMR, (400 MHz) see Figure 1. |
[ 1242156-59-7 ]
6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one
Similarity: 0.77
[ 1021298-68-9 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile
Similarity: 0.76
[ 763114-26-7 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid
Similarity: 0.67
[ 230301-83-4 ]
5-Fluoro-3,4-dihydroisoquinolin-1(2H)-one
Similarity: 0.64
[ 1021298-68-9 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile
Similarity: 0.76
[ 763114-26-7 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid
Similarity: 0.67
[ 53242-88-9 ]
4-(4-Chlorobenzyl)phthalazin-1(2H)-one
Similarity: 0.62
[ 24167-56-4 ]
4-Fluoro-N,N-dimethylbenzamide
Similarity: 0.61
[ 1242156-59-7 ]
6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one
Similarity: 0.77
[ 1021298-68-9 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile
Similarity: 0.76
[ 763114-26-7 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid
Similarity: 0.67
[ 230301-83-4 ]
5-Fluoro-3,4-dihydroisoquinolin-1(2H)-one
Similarity: 0.64
[ 27469-60-9 ]
4,4-Difluorobenzhydrylpiperazine
Similarity: 0.52
[ 5368-20-7 ]
4-Methyl-3-phenylpiperazin-2-one
Similarity: 0.52
[ 1242156-59-7 ]
6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one
Similarity: 0.77
[ 1021298-68-9 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile
Similarity: 0.76
[ 763114-26-7 ]
2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid
Similarity: 0.67
[ 53242-88-9 ]
4-(4-Chlorobenzyl)phthalazin-1(2H)-one
Similarity: 0.62