Potassium Carbonate → 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-[2-(2-methylphenoxy)ethylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1249985Notes

Reaction equation

HRID 1249985 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:38])[C:13]3[CH:18]=[CH:17][C:16]([N:19]([CH2:26][CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])C(=O)C(F)(F)F)=[CH:15][C:14]=3[O:36][CH3:37])[CH2:10][CH2:9][CH2:8][CH:7]([CH2:39][C:40]([N:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)=[O:41])[C:6]=2[CH:49]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:38])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][CH2:26][CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])=[CH:15][C:14]=3[O:36][CH3:37])[CH2:10][CH2:9][CH2:8][CH:7]([CH2:39][C:40]([N:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)=[O:41])[C:6]=2[CH:49]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 180010987-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-[N-[2-(2-methylphenoxy)ethyl]-N-trifluoroacetylamino]benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 180010327-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-[2-(2-methylphenoxy)ethylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepineYield 30.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-{N-[2-(2-methylphenoxy)ethyl]-N-trifluoroacetylamino}-benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.45 g) in methanol (20 ml) is added a solution of potassium carbonate (0.11 g) in water (5 ml), and the mixture is stirred at room temperature for 12 hours. The mixture is evaporated to remove the solvent, and thereto is added water. The mixture is extracted with ethyl acetate, and the extract is dried, evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=80:1→50:1→30:1), and recrystallized from acetone/n-hexane to give 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-[2-(2-methylphenoxy)ethylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.12 g) as white powder.

Workup

  1. customThe mixture is evaporated
  2. customto remove the solvent
  3. additionis added water
  4. extractionThe mixture is extracted with ethyl acetate
  5. customthe extract is dried
  6. customevaporated
  7. customto remove the solvent
  8. customThe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=80:1→50:1→30:1)
  9. customrecrystallized from acetone/n-hexane

Sources & evidence

ORD record
ord-cc018178e76d473ab950f5734e974bf2
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

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