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

HRID 1435978Notes

Reaction equation

HRID 1435978 reaction equation
[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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolventHCID 447138Water dimerSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3a310b1417b64731830eab74d2721522
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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