Methanol → methyl [6-chloro-2-[(5,6,7,8-tetrahydroisoquinolin-3-yl)carbonyl]-1H-indol-3-yl]acetate

HRID 380560노트

반응식

HRID 380560 반응식
[Cl:1][C:2]1[CH:13]=[CH:12][C:5](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])=[C:4]([NH2:14])[CH:3]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]1(S(Cl)(=O)=O)[CH:26]=CC=[CH:23][CH:22]=1.[CH3:31][OH:32].Cl[CH2:34]Cl>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[C:34]([C:31]([C:16]3[N:15]=[CH:20][C:19]4[CH2:26][CH2:21][CH2:22][CH2:23][C:18]=4[CH:17]=3)=[O:32])[NH:14]2)=[CH:12][CH:13]=1

참가 물질

6

반응물 5

HCID 887MethanolHCID 1049PyridineHCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 14925557Methyl (2E)-3-(2-amino-4-chlorophenyl)-2-propenoate

생성물 1

HCID 9908023methyl [6-chloro-2-[(5,6,7,8-tetrahydroisoquinolin-3-yl)carbonyl]-1H-indol-3-yl]acetate수율 76%

실험 절차

To a solution of methyl trans-4-chloro-2-aminocinnamate (R. W. Carling et al., J.Med.Chem., 1993, 36, 3397., 30.7 g, 0.15 mol) and pyridine (36 ml, 0.45 mol) in dichloromethane (500 ml) was added benzenesulfonyl chloride (20 ml, 0.16 mol). After stirring for 20 h, methanol (50 ml) was added and the mixture was concentrated. The residual solids were dissolved in dichloromethane (700 ml) and washed with 2N aqueous HCl (150 ml), brine (150 ml) and dried (MgSO4). After removal of solvent, the residual solids were recrystallized from ethanol to give 40 g (76%) of the title compound as pale yellow solids.

후처리

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residual solids were dissolved in dichloromethane (700 ml)
  3. washwashed with 2N aqueous HCl (150 ml), brine (150 ml)
  4. dry with materialdried (MgSO4)
  5. customAfter removal of solvent
  6. customthe residual solids were recrystallized from ethanol

출처 및 근거

ORD 기록
ord-ea735e3059ba4568a087031e186dec73
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303628B1

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