Triethylamine → HCID 22903474, compound

HRID 1489085Notes

Reaction equation

HRID 1489085 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:33])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:32])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][C:29](O)=[O:30])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:34]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[CH3:50][N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]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:33])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:32])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][C:29]([N:54]4[CH2:55][CH2:56][N:51]([CH3:50])[CH2:52][CH2:53]4)=[O:30])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:34]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 22903534HCID 22903534, compound

Product 1

HCID 22903474HCID 22903474, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-1-[6-(2-carboxymethoxybenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g) in dichloromethane (10 ml) is added with stirring N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.25 g) under ice-cooling, and the mixture is stirred at room temperature for 15 minutes. Subsequently, to the reaction mixture is added N-methylpiperazine (0.11 ml), and thereto is added triethylamine (0.23 ml). The mixture is stirred at room temperature overnight, and thereto is added water. The mixture is extracted with dichloromethane, and 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-1-{6-[2-(4-methyl-1-piperazinyl)carbonylmethoxybenzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (390 mg) as white powder.

Workup

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

Sources & evidence

ORD record
ord-b66a5b9d64b64209816feaeada6a8e4e
Source dataset
uspto-grants-1997_10
Patent number
US05677299

Reaction notes

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