Imidazole → HCID 19608060, compound

HRID 1291672Notes

Reaction equation

HRID 1291672 reaction equation
Cl[CH2:2][C:3]([NH:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[CH:20][CH:19]=2)[CH2:9][CH2:8][CH2:7]1)=[O:4].[NH:35]1[CH:39]=[CH:38][N:37]=[CH:36]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:35]1([CH2:2][C:3]([NH:5][CH:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]([C:17](=[O:34])[C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])=[CH:20][CH:19]=3)[CH2:9][CH2:8][CH2:7]2)=[O:4])[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 19608022HCID 19608022, compound

Product 1

HCID 19608060HCID 19608060, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixed solution of 5-(2-chloroacetylamino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.6 g), imidazole (0.1 g) and potassium carbonate (0.19 g) in acetonitrile (30 ml) is refluxed for 8 hours. The reaction solution is concentrated and the resulting residue is washed with water and separated by decantation. The remainder is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1→15:1), and recrystallized from ethanol/n-hexane to give 5-[2-(1-imidazolyl)acetylamino]-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.15 g) as colorless needles, m.p. 250°-252° C.

Workup

  1. concentrationThe reaction solution is concentrated
  2. washthe resulting residue is washed with water
  3. customseparated by decantation
  4. customThe remainder is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1→15:1)
  5. customrecrystallized from ethanol/n-hexane

Sources & evidence

ORD record
ord-678ea467779941119986c2868f1c3360
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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