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

HRID 2411443Notes

Reaction equation

HRID 2411443 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]([CH:30]4[CH2:32][CH2:31]4)=[CH:28][C:27]([CH3:33])=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[O:17])=[C:12]([F:34])[CH:11]=1>>[CH:30]1([C:29]2[C:24]([N:21]3[CH2:20][CH2:19][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[F:34])=[O:17])[CH2:23][CH2:22]3)=[N:25][CH:26]=[C:27]([CH3:33])[CH:28]=2)[CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 58484686(4-Bromo-2-fluorophenyl)[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676774(S)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252064(S)-[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl][2-fluoro-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 22.9%

Procedure

Using (S)-4-methylisothiazolidine 1,1-dioxide (203 mg) described in Preparation Example 4 and (4-bromo-2-fluorophenyl)[4-(3-cyclopropyl-5-methylpyridin-2-yl)piperazin-1-yl]methanone (418 mg) described in Preparation Example 129 and by the reaction and treatment in the same manner as in Example 4, the title compound (108 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 129 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-29e8bbf9d3ff4736a8b983b193b3f4f6
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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