Methanol → HCID 67974828, compound

HRID 1502455Notes

Reaction equation

HRID 1502455 reaction equation
F[C:2]1[C:7]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)=[C:6]([CH3:19])[CH:5]=[CH:4][N:3]=1.CO.C[O-].[Na+].[C:25](=O)(O)[O-:26].[Na+]>>[CH3:25][O:26][C:2]1[C:7]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)=[C:6]([CH3:19])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 67974724HCID 67974724, compound

Product 1

HCID 67974828HCID 67974828, compound

Conditions

Temperature
50 °C

Procedure

To a solution of 7-(2-fluoro-4-methylpyridin-3-yl)isoquinolin-3-amine (94.8 mg; 0.374 mmol) in methanol (2.0 mL; 50 mmol) was added a solution of sodium methoxide (25 mass %) in methanol (1.0 mL; 4.5 mmol). The reaction mixture was heated at 50° C. for 5 days. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted with dichloromethane (2×50 mL). The combined dichloromethane extracts were dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the title compound in quantitative yield, which was carried forward without purification. LCMS (ESI): M+H=266.2; 1H NMR (400 MHz, DMSO) δ 8.80 (s, 1H), 8.04 (d, J=5.1 Hz, 1H), 7.64 (s, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.29 (d, J=8.6 Hz, 1H), 6.98 (d, J=5.1 Hz, 1H), 6.65 (s, 1H), 5.92 (s, 2H), 3.76 (s, 3H), 2.10 (s, 3H).

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialThe combined dichloromethane extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-edcac9b4903d4771a45d561a24fa6d59
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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