Chlorine → HCID 178427167, compound

HRID 2053843Notes

Reaction equation

HRID 2053843 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][CH2:62][CH2:63][C@H:64]([NH2:75])[C:65]1[NH:69][C:68]2[CH:70]=[CH:71][C:72]([Cl:74])=[CH:73][C:67]=2[N:66]=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][CH2:62][CH2:63][C@H:64]([NH:75][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:65]1[NH:69][C:68]2[CH:70]=[CH:71][C:72]([Cl:74])=[CH:73][C:67]=2[N:66]=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 178511820HCID 178511820, compound

Product 1

HCID 178427167HCID 178427167, compoundYield 71%

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 N-[(1S)-5-(benzyloxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)pentylamine in tetrahydrofuran. Yield: 71%; Rf value: 0.53 (silica gel; dichloromethane/methanol=9:1); C33H36ClN5O4 (602.13); mass spectrum: (M+H)+=602/604 (chlorine isotope) and (M−H)−=600/602 (chlorine isotope).

Sources & evidence

ORD record
ord-71cc10fae37f4bb1894c628411053d9b
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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