Potassium Acetate → HCID 178516230, compound

HRID 1714874Notes

Reaction equation

HRID 1714874 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.CC([O-])=[O:27].[K+]>CC(O)=O.O>[F:22][C:21]([F:24])([F:23])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:4]=[N:3][C:2]([OH:27])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 57647129HCID 57647129, compound

Product 1

HCID 178516230HCID 178516230, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of 3-chloro-6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine (100 mg, 0.28 mmol) and KOAc (55 mg, 0.56 mmol) in AcOH/H2O (1:1, 2 mL) was heated at 150° C. After 3 h, the solvent was evaporated and the mixture diluted with water (2 mL), extracted with (3×2 mL) EtOAc and dried over Na2SO4. Evaporation of the solvent followed by purification Combiflash chromatography (SiO2, eluant 5% MeOH/EtOAc) afforded the desired product. 1H NMR (500 MHz, acetone-d6): δ 1.86-1.93 (m, 2H), 2.10-2.14 (m, 2H), 3.33-3.39 (m, 2H), 3.54-3.60 (m, 2H), 4.88-4.90 (m, 1H), 6.77 (d, 1H), 7.10 (t, 1H), 7.34 (d, 1H), 7.49 (d, 1H), 7.59-7.65 (m, 2H). MS (+ESI) m/z 340 (MH+).

Workup

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

Sources & evidence

ORD record
ord-ce94371ce7bb48339f9a51548327e5f8
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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