Acetic Acid → HCID 178504634, compound

HRID 2053908Notes

Reaction equation

HRID 2053908 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[C:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27])[C:5]([NH:7][C@H:8]([C:13]1[NH:17][C:16]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:15]=2[N:14]=1)[CH2:9][CH2:10][S:11][CH3:12])=[O:6].ClC1C=C(C=CC=1)C(OO)=[O:38].C(O)(=O)C.ClCl>ClCCl.ClCCl.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[C:26]([N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)=[O:27])[C:5]([NH:7][C@H:8]([C:13]1[NH:17][C:16]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:15]=2[N:14]=1)[CH2:9][CH2:10][S:11]([CH3:12])=[O:38])=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24526ChlorineHCID 70297m-Chloroperbenzoic acidHCID 1785036953-bromo-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropyl]4-(pyrrolidin-1-ylcarbonyl)benzamide

Product 1

HCID 178504634HCID 178504634, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 85 from 3-bromo-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropyl]-4-(pyrrolidin-1-ylcarbonyl)benzamide, 1 equivalent of 3-chloroperoxybenzoic acid, and glacial acetic acid in dichloromethane. Yield: 81%; Rf value: 0.20 (silica gel; dichloromethane/ethanol=9:1); C23H24BrClN4O3S (551.89); mass spectrum: (M+H)+=551/553/555 (chlorine isotope).

Sources & evidence

ORD record
ord-5eb9fc66bd9140f9ac7b3ca58fa186a7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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