Chlorine → HCID 178459168, compound

HRID 2054044Notes

Reaction equation

HRID 2054044 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][CH:16]=[CH: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.[CH2:49]([O:52][CH2:53][C@H:54]([NH2:65])[C:55]1[NH:59][C:58]2[CH:60]=[CH:61][C:62]([Cl:64])=[CH:63][C:57]=2[N:56]=1)[CH:50]=[CH2:51].ClCl>O1CCCC1.ClCCl.C(O)C>[CH2:49]([O:52][CH2:53][C@H:54]([NH:65][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([N:13]2[CH2:17][CH:16]=[CH:15][CH2:14]2)=[O:12])=[C:2]([CH3:1])[CH:3]=1)[C:55]1[NH:59][C:58]2[CH:60]=[CH:61][C:62]([Cl:64])=[CH:63][C:57]=2[N:56]=1)[CH:50]=[CH2:51]

Participants

8

Reactant 5

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118586383-Methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 178459166HCID 178459166, compound

Product 1

HCID 178459168HCID 178459168, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1R)-2-allyloxy-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 63%; Rf value: 0.60 (silica gel: dichloromethane/ethanol=9:1); C25H25ClN4O3 (464.951); mass spectrum: (M+H)+=465/467 (chlorine isotope) and (M−H)−=463/465 (chlorine isotope).

Sources & evidence

ORD record
ord-f14f302dea2846cd8fe9cb5fc1fddc6f
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…