Pyridine → N-[2,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-1H-2-indolecarboxamide

HRID 862406Notes

Reaction equation

HRID 862406 reaction equation
N1C=CC=CC=1.S(Cl)(Cl)=O.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[C:20]([OH:22])=O.[NH2:23][CH:24]1[N:30]=[C:29]([C:31]2[C:36]([O:37][CH3:38])=[CH:35][C:34]([CH3:39])=[CH:33][C:32]=2[O:40][CH3:41])[C:28]2[CH:42]=[CH:43][CH:44]=[CH:45][C:27]=2[N:26]([CH3:46])[C:25]1=[O:47]>ClCCl.O>[CH3:38][O:37][C:36]1[CH:35]=[C:34]([CH3:39])[CH:33]=[C:32]([O:40][CH3:41])[C:31]=1[C:29]1[C:28]2[CH:42]=[CH:43][CH:44]=[CH:45][C:27]=2[N:26]([CH3:46])[C:25](=[O:47])[CH:24]([NH:23][C:20]([C:12]2[NH:11][C:19]3[C:14]([CH:13]=2)=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:22])[N:30]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 72899Indole-2-carboxylic acidHCID 153796223-Amino-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one

Product 1

HCID 9805268N-[2,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-1H-2-indolecarboxamideYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

0.47 ml of pyridine is dissolved in 10 ml of dichloromethane, cooled to -5° C., and 0.68 ml of thionyl chloride is added dropwise, the mixture is stirred for 20 minutes at the same temperature and then 208 mg of indole-2-carboxylic acid are added portionwise with stirring for 30 minutes. 400 mg of 3-amino-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one are added portionwise and the reaction mixture is then allowed to return to room temperature and is stirred for 16 hours. Water is added to the reaction mixture and the precipitate formed is filtered off and dried to give white crystals of N-[2,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-1H-2-indolecarboxamide melting with decomposition at 310° C.; Yield=79%.

Workup

  1. stirringwith stirring for 30 minutes
  2. customto return to room temperature
  3. stirringis stirred for 16 hours
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. customdried

Sources & evidence

ORD record
ord-9b477179f10445aca5f7214aa5807c43
Source dataset
uspto-grants-1998_02
Patent number
US05719143

Reaction notes

Loading…