4-{4-[(1-Naphthyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride → 1-Naphthyl 2-(1-{[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

HRID 573261Notes

Reaction equation

HRID 573261 reaction equation
[Cl-].[C:2]1([O:12][C:13]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:25][CH2:24][NH2+:23][CH2:22][CH2:21]3)[S:18][CH:19]=2)=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[F:26][C:27]([F:42])([F:41])[C:28]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[N:30]([CH2:37][C:38](O)=[O:39])[N:29]=1>>[F:42][C:27]([F:26])([F:41])[C:28]1[CH:32]=[C:31]([C:33]([F:36])([F:34])[F:35])[N:30]([CH2:37][C:38]([N:23]2[CH2:24][CH2:25][CH:20]([C:17]3[S:18][CH:19]=[C:15]([C:13]([O:12][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[CH:5]=[CH:4][CH:3]=4)=[O:14])[N:16]=3)[CH2:21][CH2:22]2)=[O:39])[N:29]=1

Participants

3

Reactant 2

HCID 669115674-{4-[(1-Naphthyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chlorideHCID 866474523,5-bis-(trifluoromethyl)-1H-pyrazole-1-acetic acid

Product 1

HCID 444683741-Naphthyl 2-(1-{[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

Procedure

4-{4-[(1-Naphthyloxy)carbonyl]-1,3-thiazol-2-yl}piperidinium chloride (X-2, 375 mg) is reacted analogously to Example I-772 with [3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (288 mg). This gives, after chromatographic purification, 1-naphthyl 2-(1-{[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (356 mg, 61%).

Workup

  1. customThis gives, after chromatographic purification, 1-naphthyl 2-(1-{[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (356 mg, 61%)

Sources & evidence

ORD record
ord-6a10d033c854447cad889c2daf863ef1
Source dataset
uspto-grants-2015_05
Patent number
US09029549B2

Reaction notes

Loading…