Triethylamine → HCID 22903527, compound

HRID 1489073Notes

Reaction equation

HRID 1489073 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]([O:30][CH2:31][C:32](O)=[O:33])[C:6]=2[CH:35]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[CH3:51][N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1.C(N(CC)CC)C>ClCCl.O>[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]([O:30][CH2:31][C:32]([N:55]3[CH2:56][CH2:57][N:52]([CH3:51])[CH2:53][CH2:54]3)=[O:33])[C:6]=2[CH:35]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 22903515HCID 22903515, compound

Product 1

HCID 22903527HCID 22903527, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-5-carboxymethoxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.3 g) in dichloromethane (10 ml) is added with stirring N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.2 g) under ice-cooling, and the mixture is stirred at room temperature for 15 minutes. Subsequently, to the mixture are added with stirring N-methylpiperazine (0.09 ml) and triethylamine (0.17 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 with water, 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-[(4-methyl-1-piperazinyl)carbonylmethoxy]-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.23 g) as colorless amorphous.

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 with 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

Sources & evidence

ORD record
ord-d5bf4bea4dd3477b9c2f7c4e028a09c7
Source dataset
uspto-grants-1997_10
Patent number
US05677299

Reaction notes

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