4-(1,1-Dioxo-1,2-thiazolidin-2-yl)-2-methylbenzoic acid → [4-(3-Cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methylphenyl]methanone

HRID 2411566Notes

Reaction equation

HRID 2411566 reaction equation
[O:1]=[S:2]1(=[O:17])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[C:9]([CH3:16])[CH:8]=1.[CH:18]1([C:21]2[C:22]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=2)[CH2:20][CH2:19]1>>[CH:18]1([C:21]2[C:22]([N:31]3[CH2:36][CH2:35][N:34]([C:11]([C:10]4[CH:14]=[CH:15][C:7]([N:3]5[CH2:4][CH2:5][CH2:6][S:2]5(=[O:1])=[O:17])=[CH:8][C:9]=4[CH3:16])=[O:13])[CH2:33][CH2:32]3)=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 545952974-(1,1-Dioxo-1,2-thiazolidin-2-yl)-2-methylbenzoic acidHCID 584847721-(3-Cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazine

Product 1

HCID 71251977[4-(3-Cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methylphenyl]methanoneYield 76.8%

Procedure

Using 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methylbenzoic acid (255 mg) described in Preparation Example 29 and 1-(3-cyclopropyl-5-trifluoromethylpyridin-2-yl)piperazine (271 mg) described in Preparation Example 90 and by the reaction and treatment in the same manner as in Example 87, the title compound (390 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 90 and by the reaction and treatment in the same manner as in Example 87

Sources & evidence

ORD record
ord-40598b43f25747f59bd7d2614c078531
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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