Ethyl Acetate → HCID 57717925, compound

HRID 1984861Notes

Reaction equation

HRID 1984861 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:30]C)=[C:15]3[C:20]=2[C:19]([CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:18][C:17]([C:27]([OH:29])=[O:28])=[CH:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:30])=[C:15]3[C:20]=2[C:19]([CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[N:18][C:17]([C:27]([OH:29])=[O:28])=[CH:16]3)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 57718033HCID 57718033, compound

Product 1

HCID 57717925HCID 57717925, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirring solution of 8-(4-tert-butyl-phenyl)-1-cyclopentylmethyl-5-methoxy-isoquinoline-3-carboxylic acid (190 mg, 0.45 mmol) in 3 ml of DMF was added sodium ethane thiolate (383 mg, 4.5 mmol) and resulting mixture was heated at 120° C. for 4 h. Ethyl acetate was added (10 ml) to mixture and washed with 1 N HCl, water and brine and dried over Na2SO4. Evaporation of the solvent under vacuo gave 160 mg of the title compound as a thick liquid.

Workup

  1. customresulting mixture
  2. washwashed with 1 N HCl, water and brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent under vacuo

Sources & evidence

ORD record
ord-1f221f11a56b4341affc0f05b8121127
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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