1-(3-Methyl-5-trifluoromethylpyridin-2-yl)piperazine → (R)-[2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411555Notes

Reaction equation

HRID 2411555 reaction equation
[CH3:1][S:2]([C:5]1[CH:15]=[C:14]([N:16]2[C@H:20]([CH3:21])[CH2:19][CH2:18][S:17]2(=[O:23])=[O:22])[CH:13]=[CH:12][C:6]=1[C:7](OCC)=[O:8])(=[O:4])=[O:3].[CH3:24][C:25]1[C:26]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[N:27][CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1>>[CH3:1][S:2]([C:5]1[CH:15]=[C:14]([N:16]2[C@H:20]([CH3:21])[CH2:19][CH2:18][S:17]2(=[O:23])=[O:22])[CH:13]=[CH:12][C:6]=1[C:7]([N:38]1[CH2:39][CH2:40][N:35]([C:26]2[C:25]([CH3:24])=[CH:30][C:29]([C:31]([F:34])([F:32])[F:33])=[CH:28][N:27]=2)[CH2:36][CH2:37]1)=[O:8])(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 584847291-(3-Methyl-5-trifluoromethylpyridin-2-yl)piperazineHCID 71261164ethyl (R)-2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzoate

Product 1

HCID 71252218(R)-[2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl][4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]methanoneYield 13.9%

Procedure

Using ethyl (R)-2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoate (361 mg) described in Preparation Example 28 and 1-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazine (245 mg) described in Preparation Example 84 and by the reaction and treatment in the same manner as in Example 109, the title compound (78 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 84 and by the reaction and treatment in the same manner as in Example 109

Sources & evidence

ORD record
ord-1f5d769dc2dd4da5b83d0725596664f9
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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