Chlorine → N-[(1S)-1-(7-amino-5-chloro-1H-benzimidazol-2-yl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2053920Notes

Reaction equation

HRID 2053920 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[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.[NH2:49][C:50]1[C:55]2[NH:56][C:57]([C@@H:59]([NH2:61])[CH3:60])=[N:58][C:54]=2[CH:53]=[C:52]([Cl:62])[CH:51]=1.ClCCl.C(O)C.N.ClCl>CN(C)C=O>[NH2:49][C:50]1[C:55]2[NH:56][C:57]([C@@H:59]([NH:61][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH3:60])=[N:58][C:54]=2[CH:53]=[C:52]([Cl:62])[CH:51]=1

Participants

8

Reactant 6

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 22609213HCID 22609213, compoundHCID 178461861(1S)-1-(7-amino-5-chloro-1H-benzimidazol-2-yl)ethylamine

Product 1

HCID 178427150N-[(1S)-1-(7-amino-5-chloro-1H-benzimidazol-2-yl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(7-amino-5-chloro-1H-benzimidazol-2-yl)ethylamine in dimethylformamide. Yield: 22%; Rf value: 0.45 (silica gel; dichloromethane/ethanol/ammonia=9:1:0.1); C22H24ClN5O2 (425.92); mass spectrum: (M+H)+=426/428 (chlorine isotope).

Sources & evidence

ORD record
ord-84ddf4e429f340a8bb15ce5c6c5c9fc3
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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