(4-Bromo-2-methanesulfonylphenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone → (S)-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][2-methanesulfonyl-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

HRID 2411428Notes

Reaction equation

HRID 2411428 reaction equation
[CH3:1][C@@H:2]1[CH2:6][S:5](=[O:8])(=[O:7])[NH:4][CH2:3]1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH:31]4[CH2:33][CH2:32]4)=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[O:17])=[C:12]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:11]=1>>[CH:31]1([C:27]2[CH:28]=[C:29]([CH3:30])[C:24]([N:21]3[CH2:22][CH2:23][N:18]([C:16]([C:13]4[CH:14]=[CH:15][C:10]([N:4]5[CH2:3][C@H:2]([CH3:1])[CH2:6][S:5]5(=[O:8])=[O:7])=[CH:11][C:12]=4[S:34]([CH3:37])(=[O:36])=[O:35])=[O:17])[CH2:19][CH2:20]3)=[N:25][CH:26]=2)[CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 58484821(4-Bromo-2-methanesulfonylphenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676774(S)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252416(S)-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][2-methanesulfonyl-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 40.3%

Procedure

Using (S)-4-methylisothiazolidine 1,1-dioxide (140 mg) described in Preparation Example 4 and (4-bromo-2-methanesulfonylphenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (330 mg) described in Preparation Example 126 and by the reaction and treatment in the same manner as in Example 4, the title compound (148 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 126 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-1ff3bc26d12c4d21bda1e5aa62a04115
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…