Sodium Bicarbonate → HCID 11381836, compound

HRID 2356241Notes

Reaction equation

HRID 2356241 reaction equation
[CH2:1]([O:4][C:5]1[N:10]=[N:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH2:2][CH3:3].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:18][CH:17]=1)=O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:26][O:25][CH2:24][CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[N:11]=[C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[N:10][N:9]3[CH:13]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 105110476-Propoxypyridazin-3-amineHCID 22111344HCID 22111344, compound

Product 1

HCID 11381836HCID 11381836, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 6-propoxypyridazin-3-amine (4.50 g, 29.4 mmol), 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone (8.03 g, 29.4 mmol) and ethanol (280 mL) was heated under reflux for 2.5 hours. The mixture was cooled and sodium bicarbonate (2.50 g, 30 mmol) added. The mixture was stirred at room temperature for 15 hours, heated under reflux for 1 hour, then cooled and evaporated. The residue was extracted with chloroform (150 mL) and the extract washed with saturated, aqueous, sodium chloride solution (50 mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-2% methanol in dichloromethane afforded a green/brown solid. Treatment with decolourising charcoal in diethyl ether solution (three times) and recrystallization from cyclohexane gave Compound 63 (3.95 g, 41%) as pale green crystals. M.p. 82.5-84° C. 1H n.m.r. (CDCl3) δ 1.06, t, J=7.2 Hz, 3H; 1.75-1.94, m, 2H; 3.47, s, 3H; 3.74-3.81, m, 2H; 4.14-4.21, m, 2H; 4.27, t, J=6.6 Hz, 2H; 6.68, d, J=9.3 Hz, 1H; 7.00, d, J=8.8 Hz, 2H; 7.76-7.88, m, 3H; 7.94, s, 1H. Mass spectrum (APCI+) m/z 328 (M+H, 100%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureThe mixture was cooled
  4. temperatureheated
  5. temperatureunder reflux for 1 hour
  6. temperaturecooled
  7. customevaporated
  8. extractionThe residue was extracted with chloroform (150 mL)
  9. washthe extract washed with saturated, aqueous, sodium chloride solution (50 mL)
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe residue was purified by flash chromatography on silica gel
  13. washElution with 1-2% methanol in dichloromethane
  14. customafforded a green/brown solid
  15. customTreatment with decolourising charcoal in diethyl ether solution (three times) and recrystallization from cyclohexane

Sources & evidence

ORD record
ord-c7f679c2484f4ad9a7cf0a1fc9b8be35
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

Loading…