Diethyl Ether → HCID 89618850, compound

HRID 1502164Notes

Reaction equation

HRID 1502164 reaction equation
C([NH:7][C:8]1[N:13]=[N:12][C:11]([CH2:14][C:15]([O-:17])=[O:16])=[CH:10][CH:9]=1)(=O)C(C)(C)C.[CH3:18][Si](C=[N+]=[N-])(C)C.C(OCC)C>Cl.O>[NH2:7][C:8]1[N:13]=[N:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 131734300HCID 131734300, compound

Product 1

HCID 89618850HCID 89618850, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-(6-pivalamidopyridazin-3-yl)acetate (740 mg, 2.52 mmol) in 6 N hydrochloric acid (24 mL) was heated to 105° C. for 12 h, then cooled and concentrated in vacuo. The resulting crude residue was redissolved in methanol (10 mL) and treated dropwise with a 2 N solution of trimethylsilyldiazomethane in diethylether (2.52 mL, 5.04 mmol). After 1 h, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine, dried (sodium sulfate), filtered and concentrated to provide title compound. LC-MS (IE, m/z): 168 [M+1]+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting crude residue was redissolved in methanol (10 mL)
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b7886ccafb184b74924110e275a9b876
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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