(4-Bromo-2-fluorophenyl) [4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone → (S)-[2-fluoro-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411442Notes

Reaction equation

HRID 2411442 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]([CH3:31])=[C:26]([CH3:32])[N:25]=3)[CH2:20][CH2:19]2)=[O:17])=[C:12]([F:33])[CH:11]=1>>[F:33][C:12]1[CH:11]=[C:10]([N:4]2[CH2:3][C@H:2]([CH3:1])[CH2:6][S:5]2(=[O:8])=[O:7])[CH:15]=[CH:14][C:13]=1[C:16]([N:18]1[CH2:19][CH2:20][N:21]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[C:26]([CH3:32])[N:25]=2)[CH2:22][CH2:23]1)=[O:17]

Participants

3

Reactant 2

HCID 58484847(4-Bromo-2-fluorophenyl) [4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676774(S)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252514(S)-[2-fluoro-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanoneYield 32.4%

Procedure

Using (S)-4-methylisothiazolidine 1,1-dioxide (152 mg) described in Preparation Example 4 and (4-bromo-2-fluorophenyl)[4-(3,5,6-trimethylpyridin-2-yl)piperazin-1-yl]methanone (305 mg) described in Preparation Example 128 and by the reaction and treatment in the same manner as in Example 4, the title compound (112 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 128 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-af38f3ffd792415f84e1bd46790fe996
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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