Ammonia → 7-Pyridin-4-yl-6-{3-[3-(4-trifluoromethyl-phenyl)-ureido]-phenyl}-pyrazolo[5,1-b]thiazole-3-carboxylic acid amide

HRID 38097

Reaction equation

C([O:3][C:4]([C:6]1[N:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[O:22])[CH:15]=3)[C:11]([C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[C:8]2[S:9][CH:10]=1)=O)C.[NH3:40]>CO>[N:37]1[CH:36]=[CH:35][C:34]([C:11]2[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:26][CH:25]=4)=[O:22])[CH:15]=3)=[N:13][N:7]3[C:6]([C:4]([NH2:40])=[O:3])=[CH:10][S:9][C:8]=23)=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 60 °C

Procedure

7-Pyridin-4-yl-6-{3-[3-(4-trifluoromethyl-phenyl)-ureido]-phenyl}-pyrazolo[5,1-b]-thiazole-3-carboxylic acid ethyl ester (31 mg, 0.056 mmol) was suspended a 7 N ammonia solution in methanol (1.5 mL) in a screw cap Pyrex tube. The mixture was stirred at 60° C. for 32 hours and then allowed to cool slowly to room temperature during the night. The suspended solid was filtered, washed with DCM and dried at 50° C. under high vacuum to give 13 mg of 7-pyridin-4-yl-6-{3-[3-(4-trifluoromethyl-phenyl)-ureido]-phenyl}-pyrazolo[5,1-b]thiazole-3-carboxylic acid amide (46%) as off-white solid.

Workup

customcap Pyrex tube
temperatureto cool slowly to room temperature during the night
filtrationThe suspended solid was filtered
washwashed with DCM
customdried at 50° C. under high vacuum

Sources & evidence

ORD record: ord-3c989f9eec9e407984d3bf9a37863345
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524707B2

Linked notes

Loading…