Chlorine → HCID 178464784, compound

HRID 2053847Notes

Reaction equation

HRID 2053847 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([NH:13][CH: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(O[N:34]1N=NC2C=[CH:38][CH:39]=[CH:40][C:35]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.N1CCCC1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:25][C:23]1[CH:22]=[CH:21][C:19]2[NH:20][C:16]([CH:14]([NH:13][C:11](=[O:12])[C:9]3[CH:8]=[CH:7][C:3]([C:4]([N:34]4[CH2:35][CH2:40][CH2:39][CH2:38]4)=[O:6])=[C:2]([Cl:1])[CH:10]=3)[CH3:15])=[N:17][C:18]=2[CH:24]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178464831HCID 178464831, compound

Product 1

HCID 178464784HCID 178464784, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, TBTU, diisopropylethylamine, and pyrrolidine in tetrahydrofuran. Yield: 56%; Rf value: 0.49 (silica gel; dichloromethane/ethanol=9:1); C21H20Cl2N4O2 (431.32); mass spectrum: (M+H)+=433/433/435 (chlorine isotope).

Sources & evidence

ORD record
ord-df48b0df3ad244ecb2e0d255ce044c5c
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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