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

HRID 2366773Notes

Reaction equation

[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([F:31])=[C:21]([NH:23]C(=O)OC(C)(C)C)[CH:22]=2)[N:10]=3)=[O:5])[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+]>Cl.C(OCC)(=O)C>[NH2:23][C:21]1[CH:22]=[C:17]([NH:16][C:11]2[N:10]=[C:9]3[S:8][C:7]([NH:6][C:4]([CH:1]4[CH2:2][CH2:3]4)=[O:5])=[N:15][C:14]3=[CH:13][CH:12]=2)[CH:18]=[CH:19][C:20]=1[F:31]

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 hydrogen chloride/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 the mixture was 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 violet powder.

Workup

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

Sources & evidence

ORD record: ord-252d881ce4f4433195ea78328da9ecc9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697874B2

Reaction notes

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