Methanol → HCID 24804392, compound

HRID 1625000Notes

Reaction equation

HRID 1625000 reaction equation
C([O:4][CH2:5][CH:6]([N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:22](=[O:36])[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=2)[C:13]1=[O:37])[CH2:7][O:8]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][NH:23][C:22]([C:18]2[C:19]3[CH:20]=[CH:21][N:12]([CH:6]([CH2:7][OH:8])[CH2:5][OH:4])[C:13](=[O:37])[C:14]=3[CH:15]=[CH:16][CH:17]=2)=[O:36])=[CH:26][C:27]=1[C:32]([F:35])([F:33])[F:34]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 68347608HCID 68347608, compound

Product 1

HCID 24804392HCID 24804392, compound

Procedure

2-(5-(4-Chloro-3-(trifluoromethyl)benzylcarbamoyl)-1-oxoisoquinolin-2(1H)-yl)propane-1,3-diyl diacetate (100 mg, 0.0002 mol), potassium carbonate (80 mg, 0.0006 mol) and methanol (2 mL, 0.05 mol) were stirred at room temperature for 2 hours. The mixture was filtered and purified via flash chromatography (12 g fo silica gel, 0-10% MeOH/CH2Cl2) to give a white solid. 1H NMR (DMSO-d6) δ: 9.18 (br, 1H), 8.35 (d, J=7.6 Hz, 1H), 7.86-7.82 (m, 2H), 7.75-7.70 (m, 2H), 7.55-7.27 (m, 2H), 6.79 (d, J=7.9 Hz, 1H), 4.95-4.89 (m, 3H), 4.56 (d, J=5.9 Hz, 2H), 3.75-3.71 (m, 4H),

Workup

  1. filtrationThe mixture was filtered
  2. custompurified via flash chromatography (12 g fo silica gel, 0-10% MeOH/CH2Cl2)
  3. customto give a white solid

Sources & evidence

ORD record
ord-852702f414234090a0526341ad8ef27a
Source dataset
uspto-grants-2014_07
Patent number
US08779144B2

Reaction notes

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