Acetic Acid → HCID 67703563, compound

HRID 1377827Notes

Reaction equation

HRID 1377827 reaction equation
[CH3:1][C:2]1([C:7]2[N:12]=[N:11][C:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([N:24]4[CH2:28][N:27]=[C:26]([C:29]([F:32])([F:31])[F:30])[O:25]4)=[CH:19][C:18]=3[CH3:33])=[CH:9][CH:8]=2)OCC[O:3]1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>O>[C:2]([C:7]1[N:12]=[N:11][C:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([N:24]3[CH2:28][N:27]=[C:26]([C:29]([F:32])([F:31])[F:30])[O:25]3)=[CH:19][C:18]=2[CH3:33])=[CH:9][CH:8]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 67703562HCID 67703562, compound

Product 1

HCID 67703563HCID 67703563, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.5 g (1.08 mmol) of 6-(2-methyl-1,3-dioxolan-2-yl)-3-[3-[2,6-dimethyl-4-(5-trifluoromethyl-1,2,4-oxadiazol-2-yl)-phenoxy]-propyl]-pyridazine from example 8f, 8 mL of acetic acid, and 2 mL of water was heated to reflux. After adding acid solution, the reaction mixture was refluxed for 5 h. Upon cooling, the above reaction mixture was added to a freshly prepared sodium bicarbonate solution with stirring. The product was isolated and purified by chromatography on MPLC eluting with 30-50% ethyl acetate/hexane and recrystallized from hexane to afford 0.30 g (66%) of 6-acetyl-3-[3-[2,6-dimethyl-4-(5-trifluoromethyl-1,2,4-oxadiazol-2-yl)-phenoxy]-propyl]-pyridazine (R1, R2 =3,5-dimethyl, R3 =6-acetyl, R4 =hydrogen, R5 =5-trifluoromethyl-1,2,4-oxadiazolyl, Y=1,3-propylene), as a crystalline solid, m.p. 86°-87° C.

Workup

  1. temperaturewas heated to reflux
  2. additionAfter adding acid solution
  3. temperaturethe reaction mixture was refluxed for 5 h
  4. temperatureUpon cooling
  5. customThe product was isolated
  6. custompurified by chromatography on MPLC
  7. washeluting with 30-50% ethyl acetate/hexane
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-782920be581f4ac5b2fff51206dfc82b
Source dataset
uspto-grants-1997_09
Patent number
US05665763

Reaction notes

Loading…