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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 862406
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HRID 862406 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매

2
HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
-5 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-9b477179f10445aca5f7214aa5807c43
출처 데이터셋
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05719143

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