Ammonium Chloride → N-[4-(1-methylethyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamide

HRID 226025Notes

Reaction equation

HRID 226025 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[N:7]=[N:8][C:9]([CH3:12])=[CH:10][CH:11]=1)=[O:4].[CH:15]([Mg]Br)([CH3:17])[CH3:16].[NH4+].[Cl-]>C1COCC1.C(Cl)Cl>[CH3:16][CH:15]([C:11]1[CH:10]=[C:9]([CH3:12])[N:8]=[N:7][C:6]=1[NH:5][C:3](=[O:4])[C:2]([CH3:14])([CH3:13])[CH3:1])[CH3:17]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 688407892,2-dimethyl-N-(6-methyl-pyridazine-3-yl)-propionamideHCID 178418365HCID 178418365, compound

Product 1

HCID 68858996N-[4-(1-methylethyl)-6-methyl-pyridazin-3-yl]-2,2-dimethyl-propionamideYield 28.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,2-dimethyl-N-(6-methyl-pyridazin-3-yl)-propionamide (4.00 g, 20.73 mmol) in THF (50 mL) is stirred at 0° C. 2.0 M iPrMgBr (46.6 mL, 93.26 mmol) is then added dropwise. The reaction is stirred at 0° C. for 30 min, then it is refluxed for 2 h. It is cooled to rt, poured into ice-H2O; sat. NH4Cl is added and extracted with EtOAc; dried with Na2SO4, filtered and concentrated. The crude material is dissolved in CH2Cl2 (100 mL), treated with 12 (5.8 g, 22.80 mmol) and stirred at rt for 2 h. The reaction is diluted with CH2Cl2 (100 mL), washed with 5% Na2SO3 (3×100 mL); dried with Na2SO4, filtered and concentrated. Purification of the crude material gives the title compound (1.38 g, 5.87 mmol, 28%). ES-MS (m/z): calcd for C13H21N3O (M+H)+: 236.3. found: 236.1.

Workup

  1. temperatureit is refluxed for 2 h
  2. temperatureIt is cooled to rt
  3. extractionextracted with EtOAc
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude material is dissolved in CH2Cl2 (100 mL)
  8. stirringstirred at rt for 2 h
  9. washwashed with 5% Na2SO3 (3×100 mL)
  10. dry with materialdried with Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customPurification of the crude material

Sources & evidence

ORD record
ord-a99e2753d3b64061a9724f9660b2a285
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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