Triethylamine → HCID 178427198, compound

HRID 2053874Notes

Reaction equation

HRID 2053874 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[C:18]([CH3:29])[CH:17]=1)[C:4]1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:6]=2[N:5]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[Cl:13][C:11]1[CH:10]=[CH:9][C:7]2[NH:8][C:4]([C@@H:3]([NH:14][C:15](=[O:30])[C:16]3[CH:21]=[CH:20][C:19]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])=[C:18]([CH3:29])[CH:17]=3)[CH2:2][NH:1][S:39]([CH3:38])(=[O:41])=[O:40])=[N:5][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178427197HCID 178427197, compound

Product 1

HCID 178427198HCID 178427198, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg (0.2 mmol) of N-[(1S)-2-amino-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide is placed in 2 mL of dichloromethane, combined with 0.03 g (0.25 mmol) of triethylamine and while being cooled in the ice bath combined with 0.03 g (0.23 mmol) of methanesulfonic acid chloride. Then the mixture is heated to ambient temperature and stirred for 24 hours. Then the solvent is eliminated in vacuo and the residue purified by chromatography on silica gel (gradient: dichloromethane/methanol=100:5). Yield: 27 mg (25%); Rf value: 0.20 (silica gel; dichloromethane/methanol=95:5); C23H26ClN5O4S (504.01); mass spectrum: (M+H)+=504/506 (chlorine isotope).

Workup

  1. customthe residue purified by chromatography on silica gel (gradient: dichloromethane/methanol=100:5)

Sources & evidence

ORD record
ord-2ae494a63a7a4c4c8be30891598e6742
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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