Sodium Bicarbonate → HCID 68456328, compound

HRID 2356244Notes

Reaction equation

HRID 2356244 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[N:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[CH2:3]C1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][CH:18]=1)=O.[C:26](=O)([O-])O.[Na+]>C(O)C>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[CH2:14][N:10]3[N:11]([CH3:26])[C:6]([O:5][CH2:4][CH2:1][CH3:3])=[CH:7][CH:8]=[C:9]3[N:12]=2)=[CH:18][CH:19]=1)[CH3:25]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21130602-Bromo-1-(4-ethoxyphenyl)ethanoneHCID 68456032HCID 68456032, compound

Product 1

HCID 68456328HCID 68456328, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 6-cyclopropylmethoxypyridazin-3-amine (165 mg, 1 mmol), 2-bromo-1-(4-ethoxyphenyl)ethanone (243 mg, 1 mmol) and ethanol (10 mL) was heated under reflux for 3 hours. Sodium hydrogen carbonate (84 mg, 1 mmol) was added and the refluxing was continued for another 3 hours. The mixture was evaporated. The residue was extracted with chloroform (50 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% methanol in dichloromethane afforded Compound 33 (140 mg). 1H n.m.r. (CDCl3) δ 0.30-0.42, m, 2H; 0.60-0.74, m, 2H; 1.20-1.38, m, 1H; 1.40, t, 3H; 4.04, q, 2H; 4.14, d, 2H; 6.70, d, 1H; 6.96, d, 2H; 7.74, d, 1H; 7.80, d, 2H; 7.88, s, 1H.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe mixture was evaporated
  4. extractionThe residue was extracted with chloroform (50 mL)
  5. washthe extract washed with saturated, aqueous, sodium chloride solution (50 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel
  9. washElution with 1% methanol in dichloromethane afforded Compound 33 (140 mg)

Sources & evidence

ORD record
ord-bae948e6d5ac45dd96594862e15d5409
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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