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(S)-3-benzyloxymethylisothiazolidine 1,1-dioxide → (S)-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][4-(3-hydroxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanone

HRID 2411447
Notes
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Reaction equation

HRID 2411447 reaction equation
C([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1)C1C=CC=CC=1.Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[C:37]([CH3:38])=[CH:36][C:35]([CH:39]4[CH2:41][CH2:40]4)=[CH:34][N:33]=3)[CH2:28][CH2:27]2)=[O:25])=[C:20]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:19]=1>>[CH:39]1([C:35]2[CH:36]=[C:37]([CH3:38])[C:32]([N:29]3[CH2:30][CH2:31][N:26]([C:24]([C:21]4[CH:22]=[CH:23][C:18]([N:11]5[C@H:10]([CH2:9][OH:8])[CH2:14][CH2:13][S:12]5(=[O:15])=[O:16])=[CH:19][C:20]=4[S:42]([CH3:45])(=[O:44])=[O:43])=[O:25])[CH2:27][CH2:28]3)=[N:33][CH:34]=2)[CH2:40][CH2:41]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 16664117(S)-3-benzyloxymethylisothiazolidine 1,1-dioxideHCID 58484821(4-Bromo-2-methanesulfonylphenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 71252606(S)-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][4-(3-hydroxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanoneYield 31%

Procedure

Using (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (241 mg) described in Preparation Example 1 and (4-bromo-2-methanesulfonylphenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (478 mg) described in Preparation Example 126 and by the reaction and treatment in the same manner as in Example 32, the title compound (170 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 126 and by the reaction and treatment in the same manner as in Example 32

Sources & evidence

ORD record
ord-81ac9038ee2445ee83e3cd4899d3adcb
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08816079B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes