2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid → HCID 67156563, compound

HRID 549952Notes

Reaction equation

HRID 549952 reaction equation
Cl.[C:2]1([CH:8]([CH3:23])[CH2:9][CH2:10][CH2:11][C:12]2[N:13]=[C:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[S:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]1[N:29]([CH2:30][C:31](O)=[O:32])[N:28]=[C:27]([C:34]([F:37])([F:36])[F:35])[CH:26]=1>>[CH3:24][C:25]1[N:29]([CH2:30][C:31]([N:20]2[CH2:19][CH2:18][CH:17]([C:14]3[S:15][CH:16]=[C:12]([CH2:11][CH2:10][CH2:9][CH:8]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH3:23])[N:13]=3)[CH2:22][CH2:21]2)=[O:32])[N:28]=[C:27]([C:34]([F:36])([F:35])[F:37])[CH:26]=1

Participants

3

Reactant 2

HCID 5961182-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acidHCID 67156800HCID 67156800, compound

Product 1

HCID 67156563HCID 67156563, compound

Procedure

tert-Butyl 4-{4-[(1Z)-4-phenylpent-1-en-1-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (IV-4, 1.00 g) is dissolved in methanol and, at 40° C., hydrogenated under an H2-pressure of 10 bar in the presence of Pd/C (10%) for 5 hours. Filtration and removal of the solvent under reduced pressure gives tert-butyl 4-[4-(4-phenylpentyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (1.00 g) as a colourless oil. This is deprotected analogously to Example II-2. This gives 850 mg of 4-[4-(4-phenylpentyl)-1,3-thiazol-2-yl]piperidine hydrochloride. 169 mg are then reacted analogously to Example I-81 with [5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (100 mg). After chromatographic purification, this gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(4-phenylpentyl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (180 mg) as a colourless oil.

Workup

  1. customAfter chromatographic purification

Sources & evidence

ORD record
ord-c48e638c04f148b080bef641e9cd8827
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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