N-acetylanthranilic acid → 9-methoxy-3-(2-methyl-4-oxo-4H-quinazolin-3-yl)-1-phenyl-6,7-dihydro-3H-[1,4]diazepino [6,7,1-hi] indol-4-one

HRID 1978914

반응식

HRID 1978914 반응식
[C:1]([NH:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7](O)=[O:8])(=O)[CH3:2].[NH2:14][N:15]1[C:27](=[O:28])[C:25]2[C:26]3[N:18]([C:19]([O:29][CH3:30])=[CH:20][C:21]=3[CH2:22][CH2:23][CH:24]=2)[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:16]1.P(Cl)(Cl)Cl.[P].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:30][O:29][C:19]1[N:18]2[C:17]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:16][N:15]([N:14]3[C:7](=[O:8])[C:6]4[C:5](=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:4]=[C:1]3[CH3:2])[C:27](=[O:28])[C:25]3=[CH:24][CH2:23][CH2:22][C:21]([CH:20]=1)=[C:26]23

참가 물질

7

반응물 5

HCID 6971N-acetylanthranilic acidHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 5462309PhosphorusHCID 699571323-amino-9-methoxy-1-phenyl-6,7-dihydro-3H-[1,4]diazepino[6,7,1-hi]indol-4-one

생성물 1

HCID 699560869-methoxy-3-(2-methyl-4-oxo-4H-quinazolin-3-yl)-1-phenyl-6,7-dihydro-3H-[1,4]diazepino [6,7,1-hi] indol-4-one수율 17.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

0.834 g (4.65 mmol) of acetylanthranilic acid and 1.3 g (4.23 mmol) of 3-amino-9-methoxy-1-phenyl-6,7-dihydro-3H-[1,4]diazepino[6,7,1-hi]indol-4-one are dissolved in 13 ml of CH2Cl2, the mixture is stirred at room temperature and 0.7 g (5 mmol) of phosphorus trichloride is added. The mixture is stirred for 20 h and 0.35 g of phosphorus trichlonrde is added, followed by a fuirther 0.35 g 8 h later. The mixture is cooled, 50 ml of saturated NaHCO3 solution and 100 ml of CH2Cl2 are added and the organic phase is separated out after settling has taken place and washed with water. This solution is dried, evaporated and purified by chromatography in the mixture DM1. 0.33 g of yellow powder is obtained. M.p.=277° C.—Yld 17%.—TLC (DM3): Rf=0.47.

후처리

  1. stirringThe mixture is stirred for 20 h
  2. customfollowed by a fuirther 0.35 g 8 h
  3. temperatureThe mixture is cooled
  4. customthe organic phase is separated out after settling
  5. washwashed with water
  6. customThis solution is dried
  7. customevaporated
  8. custompurified by chromatography in the mixture DM1

출처 및 근거

ORD 기록
ord-f377b519db484db3a2f9106d17541b22
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239130B1

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