Sodium Iodide → HCID 18917235, compound

HRID 5589Notes

Reaction equation

HRID 5589 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][O:13][CH:14]2[C:20]3[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=3[N:18]([C:26](=[O:45])[C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:42])[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[CH3:41])=[CH:29][C:28]=3[O:43][CH3:44])[CH2:17][CH2:16][CH2:15]2)(=O)=O)=CC=1.[CH3:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.[I-].[Na+]>CN(C)C=O>[CH3:47][N:48]1[CH2:53][CH2:52][N:51]([CH2:11][CH2:12][O:13][CH:14]2[C:20]3[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=3[N:18]([C:26](=[O:45])[C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:42])[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[CH3:41])=[CH:29][C:28]=3[O:43][CH3:44])[CH2:17][CH2:16][CH2:15]2)[CH2:50][CH2:49]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 189171765-[2-(p-Toluenesulfonyloxy)ethoxy]-7-fluoro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 18917235HCID 18917235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[2-(p-Toluenesulfonyloxy)ethoxy]-7-fluoro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g), N-methylpiperazine (0.38 ml) and sodium iodide (0.3 g) are dispersed in dimethylformamide (10 ml), and the mixture is stirred at room temperature for 3 days. The reaction mixture is concentrated, and thereto is added water. The mixture is extracted with ethyl acetate, and the extract is dried over sodium carbonate, and purified by silica gel column chromatography (eluent; dichloromethane:methanol=10:1) to give 5-[2-(4-methyl-1-piperazinyl)-ethoxy]-7-fluoro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.15 g) as colorless amorphous.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionis added water
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe extract is dried over sodium carbonate
  5. custompurified by silica gel column chromatography (eluent; dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-09459eb81e7b4be98bb3082439814f71
Source dataset
uspto-grants-1993_09
Patent number
US05244898

Reaction notes

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