2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid → Ethyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

HRID 573242Notes

Reaction equation

HRID 573242 reaction equation
[Cl-].[CH2:2]([O:4][C:5]([C:7]1[N:8]=[C:9]([CH:12]2[CH2:17][CH2:16][NH2+:15][CH2:14][CH2:13]2)[S:10][CH:11]=1)=[O:6])[CH3:3].[F:18][C:19]([F:30])([F:29])[C:20]1[CH:24]=[CH:23][N:22]([CH2:25][C:26](O)=[O:27])[N:21]=1>>[F:30][C:19]([F:18])([F:29])[C:20]1[CH:24]=[CH:23][N:22]([CH2:25][C:26]([N:15]2[CH2:16][CH2:17][CH:12]([C:9]3[S:10][CH:11]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[N:8]=3)[CH2:13][CH2:14]2)=[O:27])[N:21]=1

Participants

3

Reactant 2

HCID 20608832-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acidHCID 178470098HCID 178470098, compound

Product 1

HCID 58242731Ethyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

Procedure

4-[4-(Ethoxycarbonyl)-1,3-thiazol-2-yl]piperidinium chloride (VI-1, 5.50 g) is reacted analogously to Example IV-1 with [3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (3.86 g). This gives, after chromatographic purification, ethyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (5.1 g, 62%).

Workup

  1. customThis gives, after chromatographic purification, ethyl 2-(1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (5.1 g, 62%)

Sources & evidence

ORD record
ord-7c5a32086aa7495cafe76cffce7e5007
Source dataset
uspto-grants-2015_05
Patent number
US09029549B2

Reaction notes

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