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

HRID 2411404Notes

Reaction equation

HRID 2411404 reaction equation
[CH:1]([C@@H:4]1[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[NH:5]1)([CH3:3])[CH3:2].Br[C:12]1[CH:17]=[CH:16][C:15]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=3)[CH2:22][CH2:21]2)=[O:19])=[C:14]([F:34])[CH:13]=1>>[CH3:32][C:31]1[C:26]([N:23]2[CH2:24][CH2:25][N:20]([C:18]([C:15]3[CH:16]=[CH:17][C:12]([N:5]4[C@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][CH2:7][S:6]4(=[O:10])=[O:9])=[CH:13][C:14]=3[F:34])=[O:19])[CH2:21][CH2:22]2)=[N:27][CH:28]=[C:29]([CH3:33])[CH:30]=1

Participants

3

Reactant 2

HCID 58484626(4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676751(S)-3-isopropylisothiazolidine 1,1-dioxide

Product 1

HCID 71252267(S)-[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl][2-fluoro-4-(3-isopropyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 16.4%

Procedure

Using (S)-3-isopropylisothiazolidine 1,1-dioxide (400 mg) described in Preparation Example 6 and (4-bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (392 mg) described in Preparation Example 114 and by the reaction and treatment in the same manner as in Example 4, the title compound (78 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 114 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-2f4e2e6d1a1d42d5aa51acbe6fb386f1
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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