Ammonia → HCID 136063610, compound

HRID 1624778Notes

Reaction equation

HRID 1624778 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=[C:3]1[CH:18]=O.N.[CH2:21]=[N:22][CH:23](S(C1C=CC(C)=CC=1)(=O)=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH:40]1CCNCC1>C1COCC1.O.C([O-])(O)=O.[Na+]>[C:24]1([C:23]2[N:22]=[CH:21][NH:40][C:18]=2[C:3]2[C:2](=[O:1])[CH:7]=[CH:6][N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)[N:4]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 4837PiperazineHCID 58072465HCID 58072465, compoundHCID 66710954HCID 66710954, compound

Product 1

HCID 136063610HCID 136063610, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carbaldehyde (129 mg, 0.479 mmol) and NH3 (30% aqueous solution, 0.168 mL, 129 mmol) in THF (1.5 mL) was stirred at room temperature for 4 h. To the mixture were added N-methylidene-1-[(4-methylphenyl)sulfonyl]-1-phenylmethanamine (131 mg, 0.479 mmol) and piperazine (41.3 mg, 0.479 mmol) at room temperature. The mixture was stirred at room temperature for 2 days. The mixture was diluted with water and saturated NaHCO3 aqueous solution, extracted with AcOEt, dried over Na2SO4, filtered, concentrated in vacuo, purified by column chromatography on basic silica gel (hexane/AcOEt=40/60 to 0/100 and AcOEt/MeOH=100/0 to 70/30) and recrystallized with AcOEt/hexane to yield the title compound (85.6 mg, 47% yield) as a pale yellow solid: NMR (DMSO-d6, 300 MHz): δ ppm 6.70 (1H, d, J=7.7 Hz), 7.22-7.44 (3H, m), 7.57-7.85 (7H, m), 8.97 (1H, d, J=8.0 Hz), 12.75 (1H, s). Anal. Calcd for C20H13F3N4O.0.7H2O: C, 60.82; H, 3.67; N, 14.19. Found: C, 60.79; H, 3.76; N, 13.84.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 days
  2. extractionextracted with AcOEt
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography on basic silica gel (hexane/AcOEt=40/60 to 0/100 and AcOEt/MeOH=100/0 to 70/30)
  7. customrecrystallized with AcOEt/hexane

Sources & evidence

ORD record
ord-d6ab9944597d419096965d63ee996dbc
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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