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

HRID 2054050Notes

Reaction equation

HRID 2054050 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.[Cl:49][C:50]1[CH:67]=[CH:66][C:53]2[NH:54][C:55]([C@@H:57]([NH2:65])[CH2:58][CH2:59][C:60]3[NH:64][N:63]=[N:62][N:61]=3)=[N:56][C:52]=2[CH:51]=1.ClCCl.C(O)C.N.ClCl>O1CCCC1>[Cl:49][C:50]1[CH:67]=[CH:66][C:53]2[NH:54][C:55]([C@@H:57]([NH:65][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH2:58][CH2:59][C:60]3[NH:64][N:63]=[N:62][N:61]=3)=[N:56][C:52]=2[CH:51]=1

Participants

8

Reactant 6

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 22609213HCID 22609213, compoundHCID 178511819(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(1H-tetrazol-5-yl)propylamine

Product 1

HCID 178427157N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(1H-tetrazol-5-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(1H-tetrazol-5-yl)propylamine in tetrahydrofuran. Yield: 37%; Rf value: 0.25 (silica gel: dichloromethane/ethanol/ammonia=9:1:0.1); C24H25ClN8O2 (492.97); mass spectrum: (M+H)+=493/495 (chlorine isotope).

Sources & evidence

ORD record
ord-2e13eb9b51694c819e724ec5a091d65d
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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