Methanol → HCID 44198699, compound

HRID 1957909Notes

Reaction equation

HRID 1957909 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:24])=[C:6]([C:17]2[CH:18]=[N:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:7]=1[C:8]1[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=1[F:16].[CH3:25][O-:26].[Na+].CO>O>[Cl:23][C:20]1[N:19]=[CH:18][C:17]([C:6]2[C:7]([C:8]3[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=3[F:16])=[C:2]([O:26][CH3:25])[N:3]=[N:4][C:5]=2[CH3:24])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 44129705HCID 44129705, compound

Product 1

HCID 44198699HCID 44198699, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloro-5-(6-chloro-pyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.a.11, 700 mg), sodium methoxide (30% solution in methanol, 750 mg) and 10 ml of methanol is heated for 6 h to 60° C. Subsequently the reaction mixture is cooled, diluted with water and extracted with ethyl acetate. The combined organic layer is washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The remainder is purified by chromatography on silica gel, using a mixture of heptane/ethyl acetate 3:1 as eluent to obtain 4-(6-chloro-pyridin-3-yl)-6-methoxy-3-methyl-5-(2,4,6-trifluoro-phenyl)-pyridazine (Compound I.a.12), m.p. 123-124° C.

Workup

  1. temperatureis heated for 6 h to 60° C
  2. temperatureSubsequently the reaction mixture is cooled
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer is washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe remainder is purified by chromatography on silica gel
  8. additiona mixture of heptane/ethyl acetate 3:1 as eluent

Sources & evidence

ORD record
ord-5d5588c4844b47b88d84e95687879996
Source dataset
uspto-grants-2013_04
Patent number
US08410026B2

Reaction notes

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