2-Methylpyrrolidine → HCID 178426209, compound

HRID 2054016Notes

Reaction equation

HRID 2054016 reaction equation
[Br: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].CN(C(O[N:34]1N=N[C:36]2[CH:37]=[CH:38][CH:39]=C[C:35]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.CC1CCCN1.BrCl>CN(C)C=O.ClCCl.C(O)C>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:34]1[CH2:35][CH2:36][CH2:37][CH:38]1[CH3:39])=[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

8

Reactant 5

HCID 130032-MethylpyrrolidineHCID 61697BROMINE CHLORIDE (BrCl)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178462082HCID 178462082, compound

Product 1

HCID 178426209HCID 178426209, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from (1S)-2-bromo-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, TBTU, diisopropylethylamine and rac.-2-methylpyrrolidine in dimethylformamide. Yield: 22%; Rf value: 0.45 (silica gel: dichloromethane/ethanol=9:1); C22H22BrClN4O2 (489.799); mass spectrum: (M+H)+=489/491/493 (bromo-chlorine isotope).

Sources & evidence

ORD record
ord-2aa6a8b0c81345ee93a196737d354933
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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