Chlorine → HCID 178427190, compound

HRID 2053784Notes

Reaction equation

HRID 2053784 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.[NH2:49][C@H:50]([C:55]1[NH:59][C:58]2[CH:60]=[CH:61][C:62]([Cl:64])=[CH:63][C:57]=2[N:56]=1)[CH2:51][C:52]([NH2:54])=[O:53].ClCl>CN(C)C=O.ClCCl.CO>[NH2:54][C:52]([CH2:51][C@H:50]([NH:49][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:55]1[NH:59][C:58]2[CH:60]=[CH:61][C:62]([Cl:64])=[CH:63][C:57]=2[N:56]=1)=[O:53]

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 178513919HCID 178513919, compound

Product 1

HCID 178427190HCID 178427190, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 10d from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (S)-3-amino-3-(5-chloro-1H-benzimidazol-2-yl)propionic acid amide in dimethylformamide. Yield: 97 mg (43% of theory); Rf value: 0.37 (silica gel; dichloromethane/methanol=9:1); C23H24ClN5O3 (453.93); mass spectrum: (M+H)+=454/456 (chlorine isotope).

Sources & evidence

ORD record
ord-1d2a19c246dc4166ac86f54fe6e2ddac
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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