Water → HCID 22903470, compound

HRID 1440288Notes

Reaction equation

HRID 1440288 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31][NH2:32])[C:6]=2[CH:33]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31][NH:32][C:34](=[O:36])[CH3:35])[C:6]=2[CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22903468HCID 22903468, compound

Product 1

HCID 22903470HCID 22903470, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-chloro-5-(2-aminoethyl)-1-[6-(2-methylbenzoyl-amino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.42 g) in pyridine (10 ml) is added acetic anhydride (0.13 ml), and the mixture is stirred at 80° C. for 2 hours, and then stirred at room temperature overnight. Water is added to the reaction solution, and the mixture is extracted with dichloromethane. The extract is washed successively with diluted hydrochloric acid, water, and aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography to give 7-chloro-5-(2-acetylamino-ethyl)-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (91 mg) as white powder.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionthe mixture is extracted with dichloromethane
  3. washThe extract is washed successively with diluted hydrochloric acid, water, and aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b30c55f8dc634c46b4b32f67ff87fd32
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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