Triethylamine → HCID 59436267, compound

HRID 1624743Notes

Reaction equation

HRID 1624743 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:8]=1)=O.Cl.[CH3:26][CH:27]([CH3:31])[CH2:28][NH:29]N.CCN(CC)CC>C(O)C.Cl>[CH3:26][CH:27]([CH3:31])[CH2:28][N:29]1[C:5]([C:7]2[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[N:8]=2)=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27609862-methylpropylhydrazine hydrochlorideHCID 667108023-[3-(dimethylamino)prop-2-enoyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one

Product 1

HCID 59436267HCID 59436267, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-[3-(dimethylamino)prop-2-enoyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (500 mg, 1.5 mmol) in ethanol (10 mL) were added 2-methylpropylhydrazine hydrochloride (274 mg, 2.2 mmol) and Et3N (0.41 mL, 3.0 mmol). The mixture was stirred at 100° C. for 5 h. The mixture was diluted with 1N HCl aqueous solution, extracted with AcOEt, washed with brine, dried over Na2SO4, concentrated in vacuo, purified by column chromatography on silica gel (hexane/AcOEt=10/90 to 0/100) and recrystallized with AcOEt/i-Pr2O to yield the title compound as a pale yellow solid (289 mg, 54%).

Workup

  1. extractionextracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography on silica gel (hexane/AcOEt=10/90 to 0/100)
  6. customrecrystallized with AcOEt/i-Pr2O

Sources & evidence

ORD record
ord-eb5f678b4b164320972a0321a63a58d2
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

Loading…