Chlorine → HCID 178427203, compound

HRID 2054079Notes

Reaction equation

HRID 2054079 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.[CH2:49]([O:56][CH2:57][C@H:58]([NH2:69])[C:59]1[NH:63][C:62]2[CH:64]=[CH:65][C:66]([Cl:68])=[CH:67][C:61]=2[N:60]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[CH2:49]([O:56][CH2:57][C@H:58]([NH:69][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[C:2]([CH3:1])[CH:3]=1)[C:59]1[NH:63][C:62]2[CH:64]=[CH:65][C:66]([Cl:68])=[CH:67][C:61]=2[N:60]=1)[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178511834HCID 178511834, compound

Product 1

HCID 178427203HCID 178427203, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1R)-2-benzyloxy-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 71%; Rf value: 0.63 (silica gel: dichloromethane/ethanol=9:1); C29H29ClN4O3 (517.03); mass spectrum: (M+H)+=517/519 (chlorine isotope).

Sources & evidence

ORD record
ord-ef4927a41f0948eea602bd0516dbde40
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…