Sodium Bicarbonate → n-[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamide

HRID 548819Notes

Reaction equation

HRID 548819 reaction equation
[C:1]([N:4]([C:8]1[N:9]=[N:10][C:11]([O:14][CH2:15][C:16]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:19][C:20]=2[CH3:21])=[CH:12][CH:13]=1)C(=O)C)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+]>CO>[CH3:21][C:20]1[O:19][N:18]=[C:17]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]=1[CH2:15][O:14][C:11]1[N:10]=[N:9][C:8]([NH:4][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67157632N-Acetyl-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamide

Product 1

HCID 67157871n-[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamideYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-acetyl-N-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-acetamide (70 mg, 0.19 mmol) in methanol (2 mL) was treated with sodium bicarbonate (1 spatula) and stirred at room temperature for 16 h. The solvent was evaporated and the residue was extracted (dichloromethane/water). The organic phase was dried over sodium sulfate and concentrated. Crystallization of the residue from diisopropylether afforded the title compound as a light brown solid (40 mg, 65%). MS: m/e=325.4 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted (dichloromethane/water)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customCrystallization of the residue from diisopropylether

Sources & evidence

ORD record
ord-ddc07c11c9ec4d7ca8a115781183c991
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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