Succinimido indolecarboxylate → cis-3-(2-indolecarboxamido)-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamide

HRID 345160Notes

Reaction equation

HRID 345160 reaction equation
[NH2:1][C@H:2]1[C@@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([NH2:22])=[O:21])[C:3]1=[O:23].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:33](ON1C(=O)CCC1=O)=[O:34]>CN(C)C=O>[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:33]([NH:1][C@H:2]1[C@@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([NH2:22])=[O:21])[C:3]1=[O:23])=[O:34]

Participants

4

Reactant 2

HCID 19993581Succinimido indolecarboxylateHCID 67931339cis-3-amino-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine 1-acetamide

Product 1

HCID 14648644cis-3-(2-indolecarboxamido)-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamideYield 102.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By conducting the reaction and treatment in the same manner as in Example 12 using 0.2 g of cis-3-amino-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine 1-acetamide and 0.1 g of succinimido 2 indolecarboxylate dissolved in 5 ml of dimethylformamide and recrystallization from a mixed solvent of ethanol and isopropyl alcohol, 0.18 g of cis-3-(2-indolecarboxamido)-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetamide 1/2 isopropyl alcohol adduct is obtained, m.p. 204°-216° C.

Workup

  1. customrecrystallization from a mixed solvent of ethanol and isopropyl alcohol

Sources & evidence

ORD record
ord-57dff4277a104c4f8aeb345e4a4df766
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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