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

HRID 2411564Notes

Reaction equation

HRID 2411564 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.Cl.[CH:19]1([C:22]2[CH:23]=[C:24]([CH3:34])[C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:26][CH:27]=2)[CH2:21][CH2:20]1>>[CH:19]1([C:22]2[CH:23]=[C:24]([CH3:34])[C:25]([N:28]3[CH2:29][CH2:30][N:31]([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])[CH2:32][CH2:33]3)=[N:26][CH:27]=2)[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 545952974-(1,1-Dioxo-1,2-thiazolidin-2-yl)-2-methylbenzoic acidHCID 673810911-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazine hydrochloride

Product 1

HCID 71253023[4-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methylphenyl]methanoneYield 16.3%

Procedure

Using 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methylbenzoic acid (255 mg) described in Preparation Example 29 and 1-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine hydrochloride (253 mg) described in Preparation Example 82 and by the reaction and treatment in the same manner as in Example 86, the title compound (74 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 82 and by the reaction and treatment in the same manner as in Example 86

Sources & evidence

ORD record
ord-1e326b1378ba414dbf3915622b3e20c6
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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