Sodium Bicarbonate → HCID 11393767, compound

HRID 2356254Notes

Reaction equation

HRID 2356254 reaction equation
[CH2:1]([S: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]([S: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 139271076-(Propylsulfanyl)pyridazin-3-amineHCID 22111344HCID 22111344, compound

Product 1

HCID 11393767HCID 11393767, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-propylsulfanylpyridazin-3-amine (169 mg, 1 mmol) and 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone (273 mg, 1 mmol) in ethanol (10 mL) was refluxed for 3 h. Sodium hydrogen carbonate (84 mg, 1 mmol) was then added and the mixture was refluxed for a further 3 h. The solvent was evaporated and the organic residue was extracted with chloroform. The chloroform extract was washed with water, dried (sodium sulfate) and evaporated. The residue was purified by radial chromatography on silica gel. Elution with 2-3% methanol in dichloromethane afforded Compound 65 (57 mg). 1H n.m.r. (CDCl3) δ 1.12, t, J=6 Hz, 3H; 1.75-1.95, m, 2H; 3.16-3.22, m, 2H; 3.27, s, 3H; 3.75-3.82, m, 2H; 4.15-4.22, m, 2H; 6.88-7.08, m, 3H; 7.80-7.995, m, 3H; 8.06, s, 1H.

Workup

  1. temperaturethe mixture was refluxed for a further 3 h
  2. customThe solvent was evaporated
  3. extractionthe organic residue was extracted with chloroform
  4. extractionThe chloroform extract
  5. washwas washed with water
  6. dry with materialdried (sodium sulfate)
  7. customevaporated
  8. customThe residue was purified by radial chromatography on silica gel
  9. washElution with 2-3% methanol in dichloromethane afforded Compound 65 (57 mg)

Sources & evidence

ORD record
ord-72bf1e5487c84db5a010480a5c7c99a8
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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