Potassium Carbonate → N-(6-Chloro-2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

HRID 418514Notes

Reaction equation

HRID 418514 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:32])[C:13]=2[NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=2)[C:8]1=[O:33])(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.CO>[Cl:32][C:12]1[C:13]([NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:29])([F:30])[F:28])[CH:21]=2)=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:33])[N:7]([CH2:6][CH2:5][OH:4])[CH:16]=[CH:15]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 595158712-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

Product 1

HCID 24760888N-(6-Chloro-2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

A round bottom flask was charged with 2-(6-chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate (80.0 mg, 0.000165 mol), potassium carbonate (34.2 mg, 0.000248 mol), methanol and 2 drops of water and the reaction was stirred for 20 minutes at room temperature. The reaction was filtered over sodium sulfate and celite and washed with methanol. The solvent was removed under reduced pressure and the residue purified by reverse phase preparative HPLC to afford the product as a pale yellow solid.

Workup

  1. filtrationThe reaction was filtered over sodium sulfate and celite
  2. washwashed with methanol
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-741c8425f59a45b7879dd7e0901bba90
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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