Sodium Bicarbonate → N-{5-[(3-amino-4-fluorophenyl)amino][1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide

HRID 1800647Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[F:30])(C)(C)C.C(=O)([O-])O.[Na+]>Cl.C(OCC)(=O)C>[NH2:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:28][CH2:29]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[F:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To tert-butyl[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}amino)-2-fluorophenyl]carbamate (3.40 g, 7.67 mmol) was added 4N hydrochloric acid/ethyl acetate (50 mL), and the mixture was stirred at 0° C. overnight. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate (50 mL×3). The organic layer was concentrated under reduced pressure to give the title compound (1.70 g, 65%) as a purple powder.

Workup

extractionextracted with ethyl acetate (50 mL×3)
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-adf88323f73a41d9be0770c5b27054bc
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344135B2

Reaction notes

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