Triethylamine → HCID 178427192, compound

HRID 2053897Notes

Reaction equation

HRID 2053897 reaction equation
[NH2:1][CH2:2][CH2:3][C@H:4]([NH:15][C:16](=[O:31])[C:17]1[CH:22]=[CH:21][C:20]([C:23]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[C:19]([CH3:30])[CH:18]=1)[C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:7]=2[N:6]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C.ClCl>ClCCl.ClCCl.C(O)C>[Cl:14][C:12]1[CH:11]=[CH:10][C:8]2[NH:9][C:5]([C@@H:4]([NH:15][C:16](=[O:31])[C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])=[C:19]([CH3:30])[CH:18]=3)[CH2:3][CH2:2][NH:1][S:33]([CH3:32])(=[O:35])=[O:34])=[N:6][C:7]=2[CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24526Chlorine2×HCID 31297Methanesulfonyl chlorideHCID 178427186HCID 178427186, compound

Product 1

HCID 178427192HCID 178427192, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 125 from N-[(1S)-3-amino-1-(5-chloro-1H-benzimidazol-2-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, methanesulfonic acid chloride, and triethylamine in dichloromethane. Yield: 37%; Rf value: 0.30 (silica gel; dichloromethane/ethanol=9:1); C24H28ClN5O4S (518.04); mass spectrum: (M+H)+=518/520 (chlorine isotope) and (M−H)−=516/518 (chlorine isotope).

Sources & evidence

ORD record
ord-e7ee45e2202b4178933d21489f6aaf0d
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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