HCID 22903480, compound → HCID 22903475, compound

HRID 1440277Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:36])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:35])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29]OS(C)(=O)=O)=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:37]=1.[C:38]1(=[O:48])[NH:42][C:41](=[O:43])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12.[K]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:36])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:35])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][N:42]4[C:41](=[O:43])[C:40]5=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]5[C:38]4=[O:48])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:37]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 7-chloro-1-{6-[2-(2-methanesulfonyloxyethoxy)-benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.75 g) in dimethylformamide (10 ml) is added potassium phthalimide (0.26 g), and the mixture is stirred at 110° C. for one hour. The mixture is poured into ice-water, and extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is purified by silica gel column chromatography to give 7-chloro-1-[6-(6,7-benzo-1-oxo-4-azepin-5-on-4-yl)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.23 g, Compound A) and 7-chloro-1-{6-[2-(2-phthalimido-ethoxy)benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.25 g, Compound B), separately.

Workup

extractionextracted with dichloromethane
washThe extract is washed with water
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9a0080576ca14606a85f39530b69fb06
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05498609

Reaction notes

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