(R)-3-methylisothiazolidine 1,1-dioxide → (R)-[2-fluoro-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411532Notes

Reaction equation

HRID 2411532 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10].[CH3:28][C@@H:29]1[CH2:33][CH2:32][S:31](=[O:35])(=[O:34])[NH:30]1>>[F:1][C:2]1[CH:7]=[C:6]([N:30]2[C@H:29]([CH3:28])[CH2:33][CH2:32][S:31]2(=[O:35])=[O:34])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10]

Participants

3

Reactant 2

HCID 16664802(R)-3-methylisothiazolidine 1,1-dioxideHCID 71252468(2-Fluoro-4-iodophenyl)[4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 71252080(R)-[2-fluoro-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]methanoneYield 5.6%

Procedure

Using (2-fluoro-4-iodophenyl)[4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]methanone (507 mg) described in Preparation Example 161 and (R)-3-methylisothiazolidine 1,1-dioxide (139 mg) described in Preparation Example 2 and by the reaction and treatment in the same manner as in Example 1, the title compound (29 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 2 and by the reaction and treatment in the same manner as in Example 1

Sources & evidence

ORD record
ord-9198820c01dd43d7a26b04b088803536
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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