Water → Citric Acid

HRID 1429857Notes

Reaction equation

HRID 1429857 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[NH2:14][C:15]1[C:20]2[C:21]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=4)=[O:32])=[CH:26][CH:25]=3)=[CH:22][S:23][C:19]=2[C:18]([C:41]2[CH:42]=[N:43][N:44]([CH2:46][CH2:47][OH:48])[CH:45]=2)=[CH:17][N:16]=1.O>CC(C)=O>[NH2:14][C:15]1[C:20]2[C:21]([C:24]3[CH:25]=[CH:26][C:27]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=4)=[O:32])=[CH:28][CH:29]=3)=[CH:22][S:23][C:19]=2[C:18]([C:41]2[CH:42]=[N:43][N:44]([CH2:46][CH2:47][OH:48])[CH:45]=2)=[CH:17][N:16]=1.[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4]

Participants

5

Reactant 2

HCID 962WaterHCID 54767922HCID 54767922, compound

Product 2

HCID 311Citric AcidHCID 46207586Ilorasertib

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In another embodiment, the invention provides a process for preparing N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea dihydrogen citrate in a solid crystalline form, wherein the crystalline form is Form I. The process comprises a) providing a mixture comprising (i) N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea, water, acetone, and citric acid; b) causing N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea dihydrogen citrate crystalline Form I to exist in the mixture. The process can further comprise isolating N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea dihydrogen citrate in a solid crystalline form, wherein the crystalline form is Form I.

Workup

  1. customIn another embodiment, the invention provides a process

Sources & evidence

ORD record
ord-3ca44147699b4d4d87f3337cb2d782e5
Source dataset
uspto-grants-2015_01
Patent number
US08940759B2

Reaction notes

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