Chlorine → HCID 178462070, compound

HRID 2054037Notes

Reaction equation

HRID 2054037 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]([OH:6])=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.[NH:57]1[CH2:61][CH2:60][CH2:59][C@@H:58]1[CH2:62][N:63]1[CH:67]=[CH:66][N:65]=[CH:64]1.ClCl>O1CCCC1.ClCCl.CO>[Cl:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:57]1[CH2:61][CH2:60][CH2:59][C@@H:58]1[CH2:62][N:63]1[CH:67]=[CH:66][N:65]=[CH:64]1)=[O:6])[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 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 280639731-{[(2R)-pyrrolidin-2-yl]methyl}-1H-imidazoleHCID 178462084(1S)-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid

Product 1

HCID 178462070HCID 178462070, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 2-chloro-4-{N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, TBTU, diisopropylethylamine, and (R)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole in tetrahydrofuran. Yield: 50%; Rf value: 0.20 (silica gel: dichloromethane/methanol=9:1); C25H24C12N6O2 (511.415); mass spectrum: (M+H)+=511/513/515 (chlorine isotope).

Sources & evidence

ORD record
ord-3845681bdf9446b2bcd3a5312255d18c
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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