Chlorine → N-[(1S)-3-(benzyloxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2053894Notes

Reaction equation

HRID 2053894 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][C:57]([NH:59][CH2:60][CH2:61][CH:62]([NH2:73])[C:63]1[NH:67][C:66]2[CH:68]=[CH:69][C:70]([Cl:72])=[CH:71][C:65]=2[N:64]=1)=[O:58])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.ClCl>O1CCCC1.ClCCl.CO>[CH2:49]([O:56][C:57]([NH:59][CH2:60][CH2:61][C@H:62]([NH:73][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:63]1[NH:67][C:66]2[CH:68]=[CH:69][C:70]([Cl:72])=[CH:71][C:65]=2[N:64]=1)=[O:58])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

8

Reactant 5

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178511137HCID 178511137, compound

Product 1

HCID 178427189N-[(1S)-3-(benzyloxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1S)-[3-(benzyloxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)propylamine in tetrahydrofuran. Yield: 87%; Rf value: 0.50 (silica gel; dichloromethane/methanol=9:1); C31H32ClN5O4 (574.08); mass spectrum: (M+H)+=574/576 (chlorine isotope) and (M−H)−=572/574 (chlorine isotope).

Sources & evidence

ORD record
ord-122313af46ce4ef4a293c9324b896b90
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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