Chlorine → 3-chloro-N-[(1S)-1-(6-chloro-1H-benzimidazol-2-yl)ethyl]-4-(pyrrolidin-1-ylsulfonyl)benzamide

HRID 2053925Notes

Reaction equation

HRID 2053925 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:13])=[O:12])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:50][C:51]1[CH:52]=[CH:53][C:54]2[N:58]=[C:57]([C@@H:59]([NH2:61])[CH3:60])[NH:56][C:55]=2[CH:62]=1.ClCl>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[S:11]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:13])=[O:12])[C:5]([NH:61][C@H:59]([C:57]1[NH:56][C:55]2[CH:62]=[C:51]([Cl:50])[CH:52]=[CH:53][C:54]=2[N:58]=1)[CH3:60])=[O:7]

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 693111543-Chloro-4-(pyrrolidin-1-ylsulfonyl)benzoic acid

Product 1

HCID 596550383-chloro-N-[(1S)-1-(6-chloro-1H-benzimidazol-2-yl)ethyl]-4-(pyrrolidin-1-ylsulfonyl)benzamideYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared analogously to Example 1g from 3-chloro-4-(pyrrolidin-1-ylsulfonyl)benzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(6-chloro-1H-benzimidazol-2-yl)ethylamine in dimethylformamide. Yield: 50%; Rf value: 0.57 (silica gel; ethyl acetate); C20H20Cl2N4O3S (467.38); mass spectrum: (M+H)+=467/469/471 (chlorine isotope).

Sources & evidence

ORD record
ord-ddab0e1e1a574be582f0b2e9011e33c3
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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