2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid → 2-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(3-phenylprop-1-yn-1-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone

HRID 549967Notes

Reaction equation

HRID 549967 reaction equation
[C:1]1([CH2:7][C:8]#[C:9][C:10]2[N:11]=[C:12]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23]C(C)(C)C)=O)[CH2:17][CH2:16]3)[S:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][C:29]1[N:33]([CH2:34]C(O)=O)[N:32]=[C:31]([C:38]([F:41])([F:40])[F:39])[CH:30]=1>>[CH3:28][C:29]1[N:33]([CH2:34][C:21]([N:18]2[CH2:17][CH2:16][CH:15]([C:12]3[S:13][CH:14]=[C:10]([C:9]#[C:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:11]=3)[CH2:20][CH2:19]2)=[O:23])[N:32]=[C:31]([C:38]([F:41])([F:39])[F:40])[CH:30]=1

Participants

3

Reactant 2

HCID 5961182-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acidHCID 67156862tert-Butyl 4-[4-(3-phenylprop-1-yn-1-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Product 1

HCID 671563492-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(3-phenylprop-1-yn-1-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone

Procedure

tert-Butyl 4-[4-(3-phenylprop-1-yn-1-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (IV-5, 320 mg) is then deprotected dann analogously to Example II-2 and then reacted analogously to Example I-81 with [5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (174 mg). After chromatographic purification, this gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(3-phenylprop-1-yn-1-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (33 mg).

Workup

  1. customAfter chromatographic purification

Sources & evidence

ORD record
ord-cfaf6503286947cd814d6c424dcaacda
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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