Hydrochloric Acid → 2-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

HRID 222730

반응식

HRID 222730 반응식
Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[CH:12]1([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][C:28]4[N:33]=[C:32]5[C:34](=[O:38])[NH:35][C:36](=[O:37])[C:31]5=[CH:30][CH:29]=4)=[CH:26][C:19]=3[CH2:18][CH2:17]2)[CH2:15][CH2:14][CH2:13]1.[BH4-].[Na+].Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.CO>[CH:12]1([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][C:28]4[N:33]=[C:32]5[CH:34]([OH:38])[NH:35][C:36](=[O:37])[C:31]5=[CH:30][CH:29]=4)=[CH:26][C:19]=3[CH2:18][CH2:17]2)[CH2:13][CH2:14][CH2:15]1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24840Magnesium perchlorateHCID 4311764Sodium borohydrideHCID 104738952-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

생성물 1

HCID 574402952-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

시약·촉매·용매 1

HCID 21584188Chloroform methanol용매

실험 절차

Magnesium perchlorate (0.89 g) was added to a solution of 2-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (E233) (0.72 g, 1.98 mmol) in a mixture of chloroform:methanol (1:1; 20 ml) at 0° C. under argon. Sodium borohydride (113 mg) was added and the mixture stirred at for 0.5 h. The mixture was adjusted to pH 2 with HCl (2M), stirred for an additional 0.5 h, then taken to pH11 with sodium hydroxide (2N). The mixture was then extracted with dichloromethane and the combined organic extracts dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90) to afford the title compound (E234); MS (ES+) m/e 366 [M+H]+.

후처리

  1. stirringstirred for an additional 0.5 h
  2. extractionThe mixture was then extracted with dichloromethane
  3. dry with materialthe combined organic extracts dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90)

출처 및 근거

ORD 기록
ord-a907f0265ffb490d9b43ee8263eba164
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207331B2

연결된 노트

불러오는 중…