Ethanol → HCID 58045983, compound

HRID 657866Notes

Reaction equation

HRID 657866 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1.[O-:16][CH2:17][CH3:18].[Na+].O.[CH2:21]([OH:23])[CH3:22]>>[CH2:17]([O:16][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1)[CH3:18].[CH2:17]([O:16][C:2]1[CH:3]=[C:4]([C:12]([O:23][CH2:21][CH3:22])([F:15])[F:13])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1)[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 2723922Sodium ethoxideHCID 58045773HCID 58045773, compound

Product 2

HCID 58045983HCID 58045983, compoundHCID 58046032HCID 58046032, compound

Conditions

Temperature
50 °C

Procedure

6-Chloro-8-trifluoromethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.004; 65 mg) was initially charged in ethanol (6 ml) and admixed with sodium ethoxide (21 mg). The reaction mixture was stirred at 50° C. for 4 h. After cooling, the mixture was admixed with water and concentrated. The residue was taken up in ethyl acetate and washed with water three times. The ethyl acetate phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by means of preparative HPLC (met. E). The product-containing fractions, each of them clean, were combined, freed of the acetonitrile, adjusted to pH 9 with sodium hydrogencarbonate and extracted three times with ethyl acetate. The combined organic extracts were dried over sodium carbonate, filtered and concentrated. 15 mg of 6-ethoxy-8-trifluoromethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine and 23 mg of 6-ethoxy-8-(ethoxydifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine were obtained.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated
  3. washwashed with water three times
  4. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by means of preparative HPLC (met. E)
  8. extractionextracted three times with ethyl acetate
  9. dry with materialThe combined organic extracts were dried over sodium carbonate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9390aae9611348148b5591b39a454fd8
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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