3-(Trifluoromethyl)aniline → ethyl 1-[(4-{[3-(trifluoromethyl)phenyl]carbamoyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

HRID 1257312Notes

Reaction equation

HRID 1257312 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[S:13][CH:14]=[C:15]([C:17]([OH:19])=O)[N:16]=2)[CH:10]=1)=[O:5])[CH3:2].[F:20][C:21]([F:30])([F:29])[C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>>[F:20][C:21]([F:29])([F:30])[C:22]1[CH:23]=[C:24]([NH:25][C:17]([C:15]2[N:16]=[C:12]([CH2:11][N:9]3[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]3)[S:13][CH:14]=2)=[O:19])[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 669392482-{[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]methyl}-1,3-thiazole-4-carboxylic acid

Product 1

HCID 66938976ethyl 1-[(4-{[3-(trifluoromethyl)phenyl]carbamoyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylateYield 86.7%

Procedure

By a reaction in the same manner as in Reference Example 19 and using the compound (281 mg, 1.00 mmol) obtained in Example 4a and 3-(trifluoromethyl)aniline (0.149 mL, 1.20 mmol), the title compound (368 mg, 86%) was obtained as a colorless oil.

Workup

  1. customBy a reaction in the same manner as in Reference Example 19

Sources & evidence

ORD record
ord-12e4f5a4c41b4ce89f0ac7d5b5d2785e
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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