2,5-Dimethoxytetrahydrofuran → HCID 19608189, compound

HRID 1603149Notes

Reaction equation

HRID 1603149 reaction equation
[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1.CO[CH:33]1[CH2:37][CH2:36][CH:35](OC)O1>C(O)(=O)C>[N:1]1([CH:2]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]([C:13](=[O:30])[C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])=[CH:16][CH:15]=3)[CH2:5][CH2:4][CH2:3]2)[CH:33]=[CH:37][CH:36]=[CH:35]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 10692311HCID 10692311, compound

Product 1

HCID 19608189HCID 19608189, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-amino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.6 g) in acetic acid (10 ml) is added dropwise 2,5-dimethoxytetrahydrofuran (0.19 ml), and the mixture is refluxed for 1 hour. The reaction solution is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1), and recrystallized from ethyl acetate/n-hexane to give 5-(1-pyrrolyl)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.31 g) as colorless prisms, m.p. 208-210° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. concentrationThe reaction solution is concentrated
  3. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1)
  4. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-7b2ae38175fc4d71becd670e4fb57134
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

Loading…