Sodium Bicarbonate → HCID 11347398, compound

HRID 2356252Notes

Reaction equation

HRID 2356252 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[CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=2)[C:14]1=O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:24][O:23][C:18]1[CH:17]=[CH:16][C:15]2[C:14]3[N:11]=[C:8]4[N:9]([C:13]=3[CH2:22][CH2:21][C:20]=2[CH:19]=1)[N:10]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=[CH:7]4

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 105110476-Propoxypyridazin-3-amineHCID 116012912-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 11347398HCID 11347398, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 6-propoxypyridazin-3-amine (120 mg, 0.78 mmol), 2-bromo-6-methoxy-3,4-dihydronaphthalen-1 (2H)-one (200 mg, 0.78 mmol) in ethanol was heated under reflux for 0.5 hours. The mixture was cooled and sodium bicarbonate (66 mg, 0.78 mmol) added. The mixture was stirred at room temperature for 3 days and evaporated. The residue was extracted with chloroform and the extract washed with saturated, aqueous, sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-2% methanol in dichloromethane afforded Compound 121 (30 mg) as a white solid. 1H n.m.r. (CDCl3) δ 1.05, t, J=7.4 Hz, 3H; 1.74-1.94, m, 2H; 3.14, s, 4H; 3.82, s, 3H; 4.28, t, J=6.8 Hz, 2H; 6.60, d, J=9.9 Hz, 1H; 6.78-6.89, m, 2H; 7.77, d, J=9.6 Hz, 1H; 7.87, d, J=7.9 Hz, 1H.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 hours
  3. temperatureThe mixture was cooled
  4. customevaporated
  5. extractionThe residue was extracted with chloroform
  6. washthe extract washed with saturated, aqueous, sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel
  10. washElution with 1-2% methanol in dichloromethane afforded Compound 121 (30 mg) as a white solid

Sources & evidence

ORD record
ord-793effb878dd4aa3b2a908a74beadb30
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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