Methanol → HCID 25012310, compound

HRID 418523Notes

Reaction equation

HRID 418523 reaction equation
C([O:4][CH2:5][C@@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:33])[C:14]=2[NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[C:23]([F:31])[CH:22]=2)[C:9]1=[O:34])[CH3:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[F:31][C:23]1[CH:22]=[C:21]([CH2:20][C:19]([NH:18][C:14]2[C:13]([CH3:33])=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[CH:17][N:8]([C@@H:6]([CH3:7])[CH2:5][OH:4])[C:9]3=[O:34])=[O:32])[CH:26]=[CH:25][C:24]=1[C:27]([F:30])([F:28])[F:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66649300HCID 66649300, compound

Product 1

HCID 25012310HCID 25012310, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round bottom flask was charged with (S)-2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)-acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (200.00 mg, 0.41803 mmol), potassium carbonate (173 mg, 0.00125 mol), methanol (15 mL, 0.37 mol) and few drops of water. The reaction was stirred at room temperature for 1 h. The reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was extracted with IPA:chloroforn, 1:3, washed with water and the solvent was removed under reduced pressure. The residue was purified by reverse phase prep HPLC to give the desired compound as light orange solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. extractionThe residue was extracted with IPA
  4. washchloroforn, 1:3, washed with water
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by reverse phase prep HPLC

Sources & evidence

ORD record
ord-7cfd803979f24ce188d25dfa91be2c88
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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