HCID 16664117, compound → HCID 86676776, compound

HRID 2411464Notes

Reaction equation

HRID 2411464 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=CC([C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[C:37]([CH:38]4[CH2:40][CH2:39]4)=[CH:36][C:35]([CH:41]4[CH2:43][CH2:42]4)=[CH:34][N:33]=3)[CH2:28][CH2:27]2)=[O:25])=NC=1>>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[N:11]1[C:37]1[C:32]([C@@H:28]2[CH2:27][N:26]([CH:24]=[O:25])[CH2:31][CH2:30][N:29]2[C:32]2[C:37]([CH:38]3[CH2:40][CH2:39]3)=[CH:36][C:35]([CH:41]3[CH2:42][CH2:43]3)=[CH:34][N:33]=2)=[N:33][CH:34]=[CH:35][CH:36]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 16664117HCID 16664117, compoundHCID 71252484HCID 71252484, compound

Product 1

HCID 86676776HCID 86676776, compoundYield 132.8%

Procedure

Using (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (287 mg) described in Preparation Example 1 and (5-bromopyridin-2-yl)[4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl]methanone (460 mg) described in Preparation Example 142 and by the reaction and treatment in the same manner as in Example 1, (S)-5-[(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)pyridin-2-yl][4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl]methanone (420 mg) was obtained. To a mixture of the obtained (S)-5-[(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)pyridin-2-yl][4-(3,5-dicyclopropylpyridin-2-yl)piperazin-1-yl]methanone (420 mg), palladium carbon (50 mg) and ammonium formate (500 mg) were added methanol (30 mL) and water (3 mL), and the mixture was stirred at 40° C. for 14 hr. Insoluble material was filtered off from the reaction mixture, and the filtrate was concentrated. To the obtained residue was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (46 mg).

Workup

  1. customdescribed in Preparation Example 142 and by the reaction and treatment in the same manner as in Example 1

Sources & evidence

ORD record
ord-f55134f90f7040a28ed6cac8ffff8f05
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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