Sodium Iodide → HCID 22903481, compound

HRID 1440284Notes

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[Cl:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31]OS(C)(=O)=O)[C:6]=2[CH:37]=1.[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.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[Cl:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[C:6]=2[CH:37]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 7-chloro-5-(2-methanesulfonyloxyethyl)-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g) in dimethylformamide (5 ml) are added pyrrolidine (0.09 ml), sodium iodide (0.14 g) and potassium carbonate (0.15 g), and the mixture is stirred at 110° C. for 2 hours. 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-[2-(1-pyrrolidinyl)ethyl]-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (98 mg) as colorless amorphous.

Workup

extractionthe mixture is extracted with dichloromethane
washThe extract is washed with water
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customto remove the solvent
customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-37d57cbe49dc4238ba78cd8b492e535e
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05498609

Reaction notes

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