Methylboronic Acid → [4-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanone

HRID 2411497Notes

Reaction equation

HRID 2411497 reaction equation
Cl[C:2]1[CH:34]=[CH:33][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:26][CH2:25][CH2:24][S:23]4(=[O:28])=[O:27])=[CH:18][C:17]=3[S:29]([CH3:32])(=[O:31])=[O:30])=[O:15])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH3:35]B(O)O>>[O:27]=[S:23]1(=[O:28])[CH2:24][CH2:25][CH2:26][N:22]1[C:19]1[CH:20]=[CH:21][C:16]([C:14]([N:11]2[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]3[CH:33]=[CH:34][C:2]([CH3:35])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[O:15])=[C:17]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:18]=1

Participants

3

Reactant 2

HCID 139377Methylboronic AcidHCID 71252067[4-(4-Chlorobenzoyl)piperidin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanone

Product 1

HCID 71252631[4-(1,1-Dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanoneYield 50.7%

Procedure

Using 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methanesulfonylbenzoic acid (138 mg) described in Preparation Example 22 and 4-(4-chlorobenzoyl)piperidine (97 mg) and by the reaction and treatment in the same manner as in Example 87, [4-(4-chlorobenzoyl)piperidin-1-yl][4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanone (76 mg) was obtained. Using the obtained [4-(4-chlorobenzoyl)piperidin-1-yl][4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanone (76 mg) and methylboronic acid (37 mg) and by the reaction and treatment in the same manner as in Example 115, the title compound (37 mg) was obtained.

Workup

  1. customby the reaction and treatment in the same manner as in Example 115

Sources & evidence

ORD record
ord-31c50ae43f4f4906af6e680bbf282952
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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