Toluene → HCID 19436793, compound

HRID 1735007Notes

Reaction equation

HRID 1735007 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]([OH:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[N:8]1.Cl[C:18]1[N:19]=[N:20][CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1.C1(C)C=CC=CC=1.N1C(C)=CC=CC=1C>ClCCl>[CH3:25][O:24][C:22]1[CH:23]=[C:18]([O:12][C:11]2[N:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[N:8]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:10]=2)[N:19]=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 79372,6-LutidineHCID 109756123-Chloro-5-methoxypyridazineHCID 178516157HCID 178516157, compound

Product 1

HCID 19436793HCID 19436793, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(Tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-5-ol (2.37 g, 0.010 mole), 3-chloro-5-methoxypyridazine (1.39 g, 0.0096 mole), toluene (60 mL), and 2,6 lutidine (1.5 g, 0.014 mole) were heated and held at reflux for 3 hours. The mixture was cooled, diluted with 100 mL of dichloromethane, and washed with 1% hydrochloric acid followed by 1% sodium hydroxide solution. The washed solution was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel using ethyl acetate/cyclohexane to give 5-methoxy-3-[[1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy]pyridazine (1.96 g, 59% yield) as a white solid.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe mixture was cooled
  3. washwashed with 1% hydrochloric acid
  4. dry with materialThe washed solution was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-56974b2d59d040e1a42320cb533d17d8
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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