4-(Trifluoromethyl)phenyl isocyanate → 1-[3-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-3-(4-trifluoromethyl-phenyl)-urea

HRID 38094

Reaction equation

HRID 38094 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:15]3[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=3)=[N:9][N:10]3[CH:14]=[CH:13][S:12][C:11]=23)=[CH:3][CH:2]=1.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]([C:15]3[CH:16]=[C:17]([NH:21][C:31]([NH:30][C:27]4[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:33])[F:34])=[CH:29][CH:28]=4)=[O:32])[CH:18]=[CH:19][CH:20]=3)=[N:9][N:10]3[CH:14]=[CH:13][S:12][C:11]=23)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 674239983-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine

Product 1

HCID 467009691-[3-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-3-(4-trifluoromethyl-phenyl)-ureaYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(7-Pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine (50 mg, 0.171 mmol) was dissolved in dry DCM (1 mL) under nitrogen atmosphere. p-trifluoromethylphenylisocyanate (0.025 mL, 0.179 mmol, 1.05 eq) was added and the mixture was stirred at room temperature for 1 hour. The solution was evaporated to dryness and the crude product was purified by chromatography on silica gel (DCM/MeOH 96:4) to give 80 mg of an oil, which after trituration with ethylether gave 63 mg of 1-[3-(7-pyridin-4-yl-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-3-(4-trifluoro-methyl-phenyl)-urea white solid (77%).

Workup

  1. customThe solution was evaporated to dryness
  2. customthe crude product was purified by chromatography on silica gel (DCM/MeOH 96:4)

Sources & evidence

ORD record
ord-c77b093748fa4d6e94c43fff8501e83b
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Linked notes

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