Acetaldehyde → HCID 59242669, compound

HRID 1485865Notes

Reaction equation

HRID 1485865 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:10]=[N:9][C:8]=2[C:19]([F:22])([F:21])[F:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:23](=O)[CH3:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCl>O1CCCC1>[CH2:23]([N:16]1[CH2:15][CH2:14][N:13]([C:11]2[N:10]=[N:9][C:8]([C:19]([F:22])([F:21])[F:20])=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:12]=2)[CH2:18][CH2:17]1)[CH3:24]

Participants

6

Reactant 4

HCID 177Acetaldehyde2×HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydride2×HCID 24880031HCID 24880031, compound

Product 1

HCID 59242669HCID 59242669, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-phenyl-6-piperazin-1-yl-3-trifluoromethyl-pyridazine (E1) (0.15 g, 0.49 mmol) in tetrahydrofuran (5 ml), was added acetaldehyde (55 ml, 0.97 mmol). The reaction mixture was stirred at room temperature for 30 min., and then sodium triacetoxyborohydride (0.154 g, 0.73 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. Then, more acetaldehyde (55 ml, 0.97 mmol) and sodium triacetoxyborohydride (0.154 g, 0.73 mmol) were added and the mixture was stirred at room temperature for 4 h. Dichloromethane was then added and the mixture was extracted with a saturated solution of ammonium chloride. The organic phase was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography (silica gel; ethyl acetate/10% ammonia in methanol (7M) in dichloromethane 10:0 to 8:2). The desired fractions were collected, the solvent evaporated in vacuo, the residue dissolved in acetonitrile and converted into its hydrochloric acid salt by addition of a saturated solution of hydrochloric acid in diethyl ether. The white solid obtained was filtered and dried affording E2 (0.039 g, 21%). C17H19F3N4.HCl; free base requires 336; Found 337 (MH+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. stirringthe mixture was stirred at room temperature for 4 h
  3. extractionthe mixture was extracted with a saturated solution of ammonium chloride
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified by column chromatography (silica gel; ethyl acetate/10% ammonia in methanol (7M) in dichloromethane 10:0 to 8:2)
  9. customThe desired fractions were collected
  10. customthe solvent evaporated in vacuo
  11. dissolutionthe residue dissolved in acetonitrile
  12. additionconverted into its hydrochloric acid salt by addition of a saturated solution of hydrochloric acid in diethyl ether
  13. customThe white solid obtained
  14. filtrationwas filtered
  15. customdried

Sources & evidence

ORD record
ord-f6f27cb9334b48a6b43211a4e5cca94b
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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