Methanol → 2-(2-Fluoro-3-(trifluoromethyl)phenyl)-N-(2-(2-hydroxyethyl)-6-(2-hydroxyethylamino)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

HRID 1161290Notes

Reaction equation

HRID 1161290 reaction equation
C([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([NH:25][C:26](=[O:39])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[C:29]=2[F:38])=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][CH2:20][O:21]C(=O)C)[CH:12]=[CH:11]2)(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[F:38][C:29]1[C:30]([C:34]([F:37])([F:36])[F:35])=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:27][C:26]([NH:25][C:9]1[C:8]([NH:7][CH2:6][CH2:5][OH:4])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]([CH2:19][CH2:20][OH:21])[C:14]2=[O:18])=[O:39]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59515734HCID 59515734, compound

Product 1

HCID 247608872-(2-Fluoro-3-(trifluoromethyl)phenyl)-N-(2-(2-hydroxyethyl)-6-(2-hydroxyethylamino)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

A round bottom flask was charged with 2-(2-(2-acetoxyethyl)-5-(2-(2-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxo-1,2-dihydroisoquinolin-6-ylamino)ethyl acetate (120 mg, 0.00022 mol), potassium carbonate (45 mg, 0.00033 mol) and methanol (3 mL, 0.07 mol) and 2 drops of water was added and the reaction stirred at room temperature for 30 minutes and was filtered over sodium sulfate and the solvent removed and the residue purified by flash chromatography to get the product as white solid. MS m/z=468.4 (M+H). 1H NMR (400 MHz ) δ 9.45 (s, 1H), 7.98 (d, J=8.95 Hz, 1H), 7.79 (t, J=7.45 Hz, 1H), 7.70 (t, J=7.09 Hz, 1H), 7.40 (t, J=7.83 Hz, 1H), 7.22 (d, J=7.83 Hz, 1H), 6.91 (d, J=9.08 Hz, 1H), 6.16 (d, J=7.73 Hz, 1H), 5.64 (t, J=5.72 Hz, 1H), 4.84 (t, J=5.33 Hz, 1H), 4.76 (t, J=5.48 Hz, 1H), 3.96 (s, 2H), 3.91 (t, J=5.27 Hz, 2H), 3.62-3.53 (m, 4H), 3.27 (q, J=6.15 Hz, 2H).

Workup

  1. additionwas added
  2. filtrationwas filtered over sodium sulfate
  3. customthe solvent removed
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-b7a516da6748416a85d39d8e8c133d5d
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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