Sodium hydride → 3-[2-(2,2-dimethyl-3-hydroxy-6-cyano-3,4-dihydro-2H-chromen-4-yl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 1590625Notes

Reaction equation

HRID 1590625 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:4][NH:3]1.[CH3:23][C:24]1([CH3:37])[CH:33]2[O:34][CH:32]2[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:35]#[N:36])[CH:30]=2)[O:25]1.[H-].[Na+]>CS(C)=O.C(OCC)(=O)C>[CH3:23][C:24]1([CH3:37])[CH:33]([OH:34])[CH:32]([N:3]2[C:2](=[O:1])[CH:7]=[CH:6][C:5]([C:8]3[C:9]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:10][N:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=34)=[N:4]2)[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:35]#[N:36])[CH:30]=2)[O:25]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-HCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 190090303-[2-(2,2-dimethyl-3-hydroxy-6-cyano-3,4-dihydro-2H-chromen-4-yl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 50.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2phenylpyrazolo[1,5-a]pyridine (0.60 g), 2,2-dimethyl-3,4-epoxy-6-cyano-3,4-dihydro-2H-chromene (0.80 g), and 60% sodium hydride (0.16 g) in dimethylsulfoxide (6 ml) was stirred for 5 hours at 60° C., and then diluted with ethyl acetate. The mixture was washed with water (10 ml) and sodium chloride aqueous solution (10 ml), dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (10 g) with a mixture of n-hexane and ethyl acetate (2:1). The fractions containing the object compound were combined and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 3-[2-(2,2-dimethyl-3-hydroxy-6-cyano-3,4-dihydro-2H-chromen-4-yl)-3-oxo-2,3-dihydropyridazin-6-yl]-2phenylpyrazolo[1,5-a]pyridine (0.51 g).

Workup

  1. washThe mixture was washed with water (10 ml) and sodium chloride aqueous solution (10 ml)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (10 g) with a mixture of n-hexane and ethyl acetate (2:1)
  5. additionThe fractions containing the object compound
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-79b5273d0bde4557acbf5ffcfb83eca6
Source dataset
uspto-grants-1993_04
Patent number
US05204346

Reaction notes

Loading…