Water → HCID 22903492, compound

HRID 1489071Notes

Reaction equation

HRID 1489071 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][C:31]([OH:33])=O)[C:6]=2[CH:34]=1.Cl.[CH3:36][NH:37][CH3:38].C(N(CC)CC)C.O>ClCCl>[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][C:31]([N:37]([CH3:38])[CH3:36])=[O:33])[C:6]=2[CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 22903486HCID 22903486, compound

Product 1

HCID 22903492HCID 22903492, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-5-carboxymethyl-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.35 g) in dichloromethane (10 ml) is added with stirring N,N-bis(2-oxo-3-oxazolydinyl)phosphinic chloride (0.24 g) under ice-cooling, and the mixture is stirred at room temperature for 15 minutes. To the mixture are added with stirring dimethylamine hydrochloride (0.078 g) and triethylamine (0.31 ml) under ice-cooling, and the mixture is 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 aqueous sodium hydroxide solution and water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography, and recrystallized from dichloromethane-diethyl ether to give 7-chloro-5-dimethylaminocarbonylmethyl-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.29 g) as white powder.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature overnight
  4. extractionthe mixture is extracted with dichloromethane
  5. washThe extract is washed successively with diluted aqueous sodium hydroxide solution and water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography
  10. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-853ebc7ae1a34d90a2beabfbab32429a
Source dataset
uspto-grants-1997_10
Patent number
US05677299

Reaction notes

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