Methanol → HCID 57940632, compound

HRID 1437309Notes

Reaction equation

HRID 1437309 reaction equation
C[Si]([N+:5]#[C-:6])(C)C.[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:18][C:17]([C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)=[O:27])=[N:16]2)=[CH:11][CH:10]=1.C[OH:35]>O1CCOCC1>[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:18][C:17]([C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][N:29]3[C:6]([NH2:5])=[O:35])=[O:27])=[N:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11674985HCID 11674985, compoundHCID 22648882Isocyano(trimethyl)silane

Product 1

HCID 57940632HCID 57940632, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Trimethylsilyl isocyanide (0.920 mL) was added to 1-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]hexahydropyridazine (0.397 g) obtained in Example 162 in 1,4-dioxane (3 mL) at room temperature, followed by stirring at an external temperature of 110° C. in a sealed tube for 4 days. Subsequently, the mixture was cooled in air. After methanol was added to the reaction mixture, the reaction solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous solution of sodium hydrogencarbonate and a mixture solvent of chloroform-methanol (20:1). The organic layer was washed with saturated brine, and then dried over sodium sulfate anhydrate. The mixture was subjected to filtration, and the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as a solid (0.122 g, 25%).

Workup

  1. temperatureSubsequently, the mixture was cooled in air
  2. customthe reaction solvent was removed under reduced pressure
  3. customThe residue was partitioned between saturated aqueous solution of sodium hydrogencarbonate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. filtrationThe mixture was subjected to filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-2eacf359db1f49d48b10dfeeca5b897b
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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