Acetic Anhydride → HCID 178474862, compound

HRID 2053873Notes

Reaction equation

HRID 2053873 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.[C:38](OC(=O)C)(=[O:40])[CH3:39]>O1CCCC1>[C:38]([NH: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)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178427197HCID 178427197, compound

Product 1

HCID 178474862HCID 178474862, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

170 mg (0.4 mmol) of (1S)—N-[2-amino-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide is placed in 3.4 mL of tetrahydrofuran, while being cooled in the ice bath with 0.1 mL (0.6 mmol) of triethylamine and then combined with 0.05 g (0.45 mmol) of acetic anhydride. 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 (gradient: dichloromethane/methanol=100:2). Yield: 23.5 mg (13%); Rf value: 0.28 (silica gel; dichloromethane/methanol=95:5); C24H26ClN5O3 (467.95); mass spectrum: (M+H)+=468/470 (chlorine isotope).

Workup

  1. customthe residue purified by chromatography (gradient: dichloromethane/methanol=100:2)

Sources & evidence

ORD record
ord-35bdec269a9f437ea2c89330b0affe96
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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