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

HRID 549966

Reaction equation

HRID 549966 reaction equation
[C:1]1([C:11]#[C:12][C:13]2[N:14]=[C:15]([CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[S:16][CH:17]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:31][C:32]1[N:36]([CH2:37][C:38]([OH:40])=O)[N:35]=[C:34]([C:41]([F:44])([F:43])[F:42])[CH:33]=1>>[CH3:31][C:32]1[N:36]([CH2:37][C:38]([N:21]2[CH2:22][CH2:23][CH:18]([C:15]3[S:16][CH:17]=[C:13]([C:12]#[C:11][C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[N:14]=3)[CH2:19][CH2:20]2)=[O:40])[N:35]=[C:34]([C:41]([F:44])([F:43])[F:42])[CH:33]=1

Participants

3

Reactant 2

HCID 5961182-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acidHCID 67157278tert-Butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Product 1

HCID 671561522-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone

Procedure

tert-Butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (IV-6, 200 mg) is deprotected analogously to Example II-2 and then reacted analogously to Example I-81 with [5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (117 mg). After chromatographic purification, this gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (112 mg).

Workup

  1. customAfter chromatographic purification

Sources & evidence

ORD record
ord-91f2b931bc854e8e87800e9e8a343b8c
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Linked notes

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