Triethylamine → HCID 59436182, compound

HRID 1624744Notes

Reaction equation

HRID 1624744 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.[NH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)N.CCN(CC)CC>C(O)C.O>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:25]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 786452-HydrazinopyridineHCID 667108023-[3-(dimethylamino)prop-2-enoyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one

Product 1

HCID 59436182HCID 59436182, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-[3-(dimethylamino)prop-2-enoyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (800 mg, 2.4 mmol) in ethanol (20 mL) were added 2-hydrazinopyridine (388 mg, 3.6 mmol) and Et3N (0.66 mL, 4.7 mmol). The mixture was stirred at 100° C. for 5 h. The mixture was diluted with water, extracted with AcOEt, washed with brine, dried over Na2SO4, concentrated in vacuo, purified by HPLC and recrystallized with AcOEt/hexane to yield the title compound as a pale yellow solid (460 mg, 51%).

Workup

  1. extractionextracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by HPLC
  6. customrecrystallized with AcOEt/hexane

Sources & evidence

ORD record
ord-e73d6cbc62f04771adaff9a7c39bd94e
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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