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

HRID 2411435Notes

Reaction equation

HRID 2411435 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]([F:34])[CH:11]=1>>[CH:31]1([C:27]2[CH:28]=[C:29]([CH3:30])[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]=2)[CH2:32][CH2:33]1

Participants

3

Reactant 2

HCID 58484842(4-Bromo-2-fluorophenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanoneHCID 86676775(R)-4-methylisothiazolidine 1,1-dioxide

Product 1

HCID 71252945(R)-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][2-fluoro-4-(4-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 34.4%

Procedure

Using (R)-4-methylisothiazolidine 1,1-dioxide (180 mg) described in Preparation Example 7 and (4-bromo-2-fluorophenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (371 mg) described in Preparation Example 121 and by the reaction and treatment in the same manner as in Example 4, the title compound (144 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 121 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-44858d2a07924afa904d148aae9dd9d0
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…