2-(5-Chloro-7-aminoindolin-1-yl)benzamide → 4-Chloro-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

HRID 3992

반응식

HRID 3992 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9](N)[CH:10]=1)[N:7]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15])[CH2:6][CH2:5]2>CO.ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:16][C:14](=[O:15])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[N:7]3[CH2:6][CH2:5][C:4]([CH:3]=1)=[C:8]23

참가 물질

3

반응물 1

HCID 138232702-(5-Chloro-7-aminoindolin-1-yl)benzamide

생성물 1

HCID 138232714-Chloro-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

2-(5-chloro-7-aminoindolin-1-yl)benzamide of Example 1c (28.7 g, 0.10 mole) was dissolved in methanol/dichloromethane (DCM) solution (1:9 v/v) at 35° C. Silica gel (510 gm) was added to absorb the starting material, then the solvent was removed as much as possible under vacuum (50° C., 25 mmHg pressure for 1 hr.) The reaction mixture was then heated at 145°-155° C. and mechanically stirred for 11/2 hours. The heating was stopped when the mixture started to turn brown. The combined material was placed onto a flash chromatography column (1 kg, silica gel 60, slurry packed with DCM), eluted with DCM (16 l) and 2% CH3OH in DCM (10 l). The fractions containing the desired product were pooled and concentrated to yield a solid, 16 gm, (59%), m.p. 252°-255° C.

후처리

  1. additionSilica gel (510 gm) was added
  2. customto absorb the starting material
  3. customthe solvent was removed as much as possible under vacuum (50° C., 25 mmHg pressure for 1 hr.) The reaction mixture
  4. temperaturewas then heated at 145°-155° C.
  5. washeluted with DCM (16 l) and 2% CH3OH in DCM (10 l)
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated
  8. customto yield a solid, 16 gm, (59%), m.p. 252°-255° C.

출처 및 근거

ORD 기록
ord-4bbfa46f3e4e40cb90638913d3ea938d
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723007

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