Ethyl Acetate → N-(6-mercaptoisoquinolin-1-yl)benzamide

HRID 1366745노트

반응식

HRID 1366745 반응식
[OH-].[Na+].[C:3]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]C(=O)N(C)C)=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>O.O.CO.C1COCC1.CCCCCCC>[SH:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[C:12]([NH:11][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[N:13][CH:14]=[CH:15]2

참가 물질

8

반응물 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86612976dimethylthiocarbamic acid S-(1-benzoylaminoisoquinolin-6-yl)ester

생성물 1

HCID 136378996N-(6-mercaptoisoquinolin-1-yl)benzamide수율 53.7%

시약·촉매·용매 4

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8900Heptane용매HCID 447138Water dimer용매

실험 절차

A solution of NaOH (92 mg) in water H2O (1 ml) was added to a solution of dimethylthiocarbamic acid S-(1-benzoylaminoisoquinolin-6-yl)ester (70 mg) in MeOH (1 ml) and THF (1 ml). The mixture was stirred for 1 h at ambient temperature then for a further 1 h at 56° C. The organics were removed in vacuo then the mixture was diluted with water and acidified with dilute hydrochloric acid (pH˜3.5). The mixture was extracted with ethyl acetate (X3), dried (sodium sulphate) and concentrated in vacuo to give a residue. Flash chromatography of the residue (eluent: 1-5% ethyl acetate in heptane) gave N-(6-mercaptoisoquinolin-1-yl)-benzamide (30 mg).

후처리

  1. waitfor a further 1 h at 56° C
  2. customThe organics were removed in vacuo
  3. additionthe mixture was diluted with water
  4. extractionThe mixture was extracted with ethyl acetate (X3)
  5. dry with materialdried (sodium sulphate)
  6. concentrationconcentrated in vacuo
  7. customto give a residue

출처 및 근거

ORD 기록
ord-1f4c81053dbd453ebe5b477757186187
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893088B2

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