3,3-Dimethyl-1-butanol → 3,3-Dimethylbutyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

HRID 573253Notes

Reaction equation

HRID 573253 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[S:18][CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=3)[CH2:13][CH2:12]2)=[O:10])[N:4]=1.[CH3:27][C:28]([CH3:33])([CH3:32])[CH2:29][CH2:30]O>>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[S:18][CH:19]=[C:20]([C:22]([O:24][CH2:30][CH2:29][C:28]([CH3:33])([CH3:32])[CH3:27])=[O:23])[N:21]=3)[CH2:13][CH2:12]2)=[O:10])[N:4]=1

Participants

3

Reactant 2

HCID 122333,3-Dimethyl-1-butanolHCID 669114762-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylic acid

Product 1

HCID 669114853,3-Dimethylbutyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

Procedure

A solution of 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylic acid (III-2, 200 mg) is reacted analogously to Example I-811 with 3,3-dimethylbutan-1-ol (68.0 mg). This gives, after chromatographic purification, 3,3-dimethylbutyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (98 mg, 40%).

Workup

  1. customThis gives, after chromatographic purification, 3,3-dimethylbutyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (98 mg, 40%)

Sources & evidence

ORD record
ord-4c095b43dca648b496b1587e39a2dc10
Source dataset
uspto-grants-2015_05
Patent number
US09029549B2

Reaction notes

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