(S)-3-benzyloxymethylisothiazolidine 1,1-dioxide → (S)-[4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl][2-fluoro-4-(3-hydroxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

HRID 2411423Notes

Reaction equation

HRID 2411423 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.[CH:17]1([C:20]2[C:21]([N:29]3[CH2:34][CH2:33][N:32]([C:35]([C:37]4[CH:42]=[CH:41][C:40](I)=[CH:39][C:38]=4[F:44])=[O:36])[CH2:31][CH2:30]3)=[N:22][CH:23]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[CH:25]=2)[CH2:19][CH2:18]1>>[CH:17]1([C:20]2[C:21]([N:29]3[CH2:30][CH2:31][N:32]([C:35]([C:37]4[CH:42]=[CH:41][C:40]([N:11]5[C@H:10]([CH2:9][OH:8])[CH2:14][CH2:13][S:12]5(=[O:15])=[O:16])=[CH:39][C:38]=4[F:44])=[O:36])[CH2:33][CH2:34]3)=[N:22][CH:23]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[CH:25]=2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 16664117(S)-3-benzyloxymethylisothiazolidine 1,1-dioxideHCID 71251940HCID 71251940, compound

Product 1

HCID 71252943(S)-[4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl][2-fluoro-4-(3-hydroxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanoneYield 43.6%

Procedure

Using (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (393 mg) described in Preparation Example 1 and [4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl](2-fluoro-4-iodophenyl)methanone (800 mg) described in Preparation Example 164 and by the reaction and treatment in the same manner as in Example 32, the title compound (365 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 164 and by the reaction and treatment in the same manner as in Example 32

Sources & evidence

ORD record
ord-9caac7d17dd24736a37f84d486521917
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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