(6-Bromopyridin-3-yl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone → (S)-[4-(4-chlorobenzoyl)piperidin-1-yl][6-(3-isopropyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)pyridin-3-yl]methanone

HRID 2411400Notes

Reaction equation

HRID 2411400 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[N:17]=[CH:16][C:15]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26](=[O:34])[C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[CH2:22][CH2:21]2)=[O:19])=[CH:14][CH:13]=1>>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:26]([CH:23]2[CH2:22][CH2:21][N:20]([C:18]([C:15]3[CH:16]=[N: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][CH:14]=3)=[O:19])[CH2:25][CH2:24]2)=[O:34])=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 58484839(6-Bromopyridin-3-yl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanoneHCID 86676751(S)-3-isopropylisothiazolidine 1,1-dioxide

Product 1

HCID 71252599(S)-[4-(4-chlorobenzoyl)piperidin-1-yl][6-(3-isopropyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)pyridin-3-yl]methanoneYield 25.7%

Procedure

Using (S)-3-isopropylisothiazolidine 1,1-dioxide (320 mg) described in Preparation Example 6 and (6-bromopyridin-3-yl)[4-(4-chlorobenzoyl)piperidin-1-yl]methanone (408 mg) described in Preparation Example 190 and by the reaction and treatment in the same manner as in Example 4, the title compound (126 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 190 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-3024547ced0a4d2881535ab885f3b7f2
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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