p-Fluorotoluene-alpha-thiol → S-(4-Fluorobenzyl) 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbothioate

HRID 573254Notes

Reaction equation

HRID 573254 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[S:17][CH:18]=[C:19]([C:21]([OH:23])=O)[N:20]=3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][SH:36])=[CH:31][CH:30]=1>>[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]3[S:17][CH:18]=[C:19]([C:21](=[O:23])[S:36][CH2:35][C:32]4[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=4)[N:20]=3)[CH2:14][CH2:15]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1

Participants

3

Reactant 2

HCID 85171p-Fluorotoluene-alpha-thiolHCID 666014572-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylic acid

Product 1

HCID 86652911S-(4-Fluorobenzyl) 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbothioate

Procedure

A solution of 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylic acid (III-4, 200 mg) is reacted analogously to Example I-227 with (4-fluorophenyl)methanethiol (78.0 mg). This gives, after chromatographic purification, S-(4-fluorobenzyl) 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbothioate (110 mg, 42%).

Workup

  1. customThis gives, after chromatographic purification, S-(4-fluorobenzyl) 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbothioate (110 mg, 42%)

Sources & evidence

ORD record
ord-be564886baaa4339b0fe82d4f1145606
Source dataset
uspto-grants-2015_05
Patent number
US09029549B2

Reaction notes

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