Methanol → (R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

HRID 1161287Notes

Reaction equation

HRID 1161287 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 59515877(R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 25013922(R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

A round bottom flask was charged with (R)-2-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (300.00 mg, 6.2704E-4 mol), potassium carbonate (260 mg, 0.0019 mol), methanol (20 mL, 0.4 mol) and 2 drops of water. The reaction was stirred at room temperature for 20 minutes. The solvent was removed and the reaction mixture was extracted with ethyl acetate and the solvent was removed to obtain the product as a light yellow solid. MS m/z=437.5 (M+H). 1H NMR (400 MHz, DMSO-d6): δ 9.91 (s, 1H), 8.07 (d, J=8.45 Hz, 1H), 7.79 (t, J=7.85 Hz, 1H), 7.53 (d, J=12.68 Hz, 1H), 7.45 (d, J=7.85 Hz, 2H), 7.37 (d, J=8.45 Hz, 1H), 6.44 (d, J=7.66 Hz, 1H), 5.05-5.00 (m, 1H), 4.93 (t, J=5.66 Hz, 1H), 3.92 (s, 2H), 3.67-3.51 (m, 2H), 2.22 (s, 3H), 1.28 (d, J=7.51 Hz, 3H).

Workup

  1. customThe solvent was removed
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-f406502d540c4662ad0c4d573a765fd9
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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