3-Amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide → 2-(p-Chlorophenyl)-3-(2-indolecarboxamido)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide

HRID 345152Notes

Reaction equation

HRID 345152 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([NH2:13])=[O:12])[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[S:4][CH:3]1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[C:34](ON1C(=O)CCC1=O)=[O:35]>CN(C)C=O>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([CH:3]2[CH:2]([NH:1][C:34]([C:26]3[NH:25][C:33]4[C:28]([CH:27]=3)=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:35])[C:8](=[O:9])[N:7]([CH2:10][C:11]([NH2:13])=[O:12])[C:6]3[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=3[S:4]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 146486333-Amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamideHCID 19993581Succinimido indolecarboxylate

Product 1

HCID 146486342-(p-Chlorophenyl)-3-(2-indolecarboxamido)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamideYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

In 30 ml of dimethylformamide are dissolved 0.9 g of 3-amino-2-(p-chlorophenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine- 5-acetamide and 1.2 g of succinimido 2-indolecarboxylate, and the solution is stirred at 65° C. for 13 hours. The reaction mixture is concentrated under reduced pressure and a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate are added to the residue. The mixture is stirred for a while. The resulting crystals are collected by filtration, and the crystals are recrystallized from a mixed solvent of chloroform and methanol to give 0.8 g of 2-(p-chlorophenyl)-3-(2-indolecarboxamido)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetamide, m.p. 275°-290° C. (decomposition).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate are added to the residue
  3. stirringThe mixture is stirred for a while
  4. filtrationThe resulting crystals are collected by filtration
  5. customthe crystals are recrystallized from a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-d156364644fd411b86b8bd179d79f373
Source dataset
uspto-grants-1991_10
Patent number
US05055464

Reaction notes

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