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

HRID 1435978ノート

反応式

HRID 1435978 の反応式
[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

参加物

8

反応物 3

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

生成物 1

HCID 136378996N-(6-mercaptoisoquinolin-1-yl)benzamide

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8900Heptane溶媒HCID 447138Water dimer溶媒

実験手順

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 as a yellow residue (30 mg).

後処理

  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

出典と根拠

ORDレコード
ord-3a310b1417b64731830eab74d2721522
出典データセット
uspto-grants-2009_11
特許番号
US07618985B2

反応ノート

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