Water → HCID 19009036, compound

HRID 1742290Notes

Reaction equation

HRID 1742290 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]2[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=23)=[N:8]1.[C-:29]#[N:30].[Na+].O>CS(C)=O>[C:29]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]2[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=23)=[N:8]1)#[N:30]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 19009005HCID 19009005, compound

Product 1

HCID 19009036HCID 19009036, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-[2-(5-bromopentyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2.753 g) and sodium cyanide (0.37 g) in dimethyl sulfoxide (12.6 ml) was stirred at room temperature for 2 hours and then at 60° C. for 1 hour. To the mixture was added water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of chloroform and methanol as an eluent to afford 3-[2-(5-cyanopentyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (1.75 g).

Workup

  1. waitat 60° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-f664b9d170d840ca961f921c4a5c3f90
Source dataset
uspto-grants-1994_08
Patent number
US05338743

Reaction notes

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