Chlorine → 3-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-4-(3-oxo-[1,4]diazepan-1-ylcarbonyl)benzamide

HRID 2054072Notes

Reaction equation

HRID 2054072 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([NH:13][C@H:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[N:17]=2)[CH3:15])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(C(C)C)CC)(C)C.[NH:35]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37][C:36]1=[O:42].ClCl>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:38]1[CH2:39][CH2:40][CH2:41][NH:35][C:36](=[O:42])[CH2:37]1)=[O:5])[C:11]([NH:13][C@H:14]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=2[N:17]=1)[CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 134285321,4-Diazepan-2-oneHCID 178462084(1S)-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid

Product 1

HCID 1784620763-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-4-(3-oxo-[1,4]diazepan-1-ylcarbonyl)benzamideYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1d from (1S)-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, PFTU, diisopropylethylamine, and [1,4]diazepan-2-one in dimethylformamide. Yield: 63%; C22H21Cl2N5O3 (474.346); mass spectrum: (M+H)+=474/476 (chlorine isotope).

Sources & evidence

ORD record
ord-a2f1e51682414873b25dc1608c0234cc
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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