Sodium Methoxide → HCID 57647143, compound

HRID 1714873Notes

Reaction equation

HRID 1714873 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[CH3:25][O-:26].[Na+]>CO>[CH3:25][O:26][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57647129HCID 57647129, compound

Product 1

HCID 57647143HCID 57647143, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-chloro-6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine (150 mg, 0.42 mmol) in MeOH (1 mL) and NaOMe (2.5 mL, 0.87 mmol, 25-30% in MeOH) was heated at 80° C. After 4 h, solvent was evaporated and the mixture was diluted with water (3 mL), extracted with EtOAc (3×2 mL) and dried over Na2SO4. Evaporation of the solvent followed by purification Combiflash chromatography (SiO2, eluant 30-40% EtOAc/hexanes) afforded the desired product. 1H NMR (500 MHz, acetone-d6): δ 1.87-1.95 (m, 2H), 2.07-2.14 (m, 2H), 3.58-3.64 (m, 2H), 3.78-3.86 (m, 2H), 3.97 (s, 3H), 4.90-5.00 (m, 1H), 6.94 (d, 1H), 7.08-7.12 (m, 1H), 7.35 (t, 2H), 7.59-7.65 (m, 2H). MS (+ESI) m/z 354 (MH+).

Workup

  1. customsolvent was evaporated
  2. additionthe mixture was diluted with water (3 mL)
  3. extractionextracted with EtOAc (3×2 mL)
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent
  6. customfollowed by purification Combiflash chromatography (SiO2, eluant 30-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-07f82f21a11b406f9dc04bd6e4144bc7
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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