Ammonia → 6-[3-(2,5-Difluoro-benzenesulfonylamino)-phenyl]-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid amide

HRID 38098Notes

Reaction equation

HRID 38098 reaction equation
C(O[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][S:21]([C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=4[F:31])(=[O:23])=[O:22])[CH:15]=3)[C:11]([C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)=[C:8]2[S:9][CH:10]=1)=[O:5])C.[NH3:38]>CO>[F:31][C:25]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=1[S:21]([NH:20][C:16]1[CH:15]=[C:14]([C:12]2[C:11]([C:32]3[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=3)=[C:8]3[S:9][CH:10]=[C:6]([C:4]([NH2:38])=[O:5])[N:7]3[N:13]=2)[CH:19]=[CH:18][CH:17]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 674218916-[3-(2,5-Difluoro-benzenesulfonylamino)-phenyl]-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid ethyl ester

Product 1

HCID 467019716-[3-(2,5-Difluoro-benzenesulfonylamino)-phenyl]-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid amideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[3-(2,5-Difluoro-benzenesulfonylamino)-phenyl]-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid ethyl ester (30 mg, 0.055 mmol) was suspended a 7 N ammonia solution in methanol (1 mL) at 0° C. and stirred at this temperature for 18 hours. The mixture was evaporated to dryness and taken up with DCM and evaporated to dryness three times. The beige solid was dried under vacuum at room temperature to give 26 mg (93%) of 6-[3-(2,5-difluoro-benzenesulfonylamino)-phenyl]-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole-3-carboxylic acid amide.

Workup

  1. customat 0° C.
  2. customThe mixture was evaporated to dryness
  3. customevaporated to dryness three times
  4. customThe beige solid was dried under vacuum at room temperature

Sources & evidence

ORD record
ord-9a871aeb26894528ad7380098e3fea80
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

Loading…