Water → HCID 67618154, compound

HRID 862486Notes

Reaction equation

HRID 862486 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:15][O:16][CH3:17])([CH2:12][O:13][CH3:14])[C@@H:9]([OH:18])[C@H:8]([NH:19][C:20]3[CH:25]=[CH:24][C:23](=[O:26])[NH:22][N:21]=3)[C:7]=2[CH:27]=1)#[N:2].[C:28](#[N:31])[CH:29]=[CH2:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:12][O:13][CH3:14])([CH2:15][O:16][CH3:17])[C@@H:9]([OH:18])[C@H:8]([NH:19][C:20]3[CH:25]=[CH:24][C:23](=[O:26])[N:22]([CH2:30][CH2:29][C:28]#[N:31])[N:21]=3)[C:7]=2[CH:27]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7855AcrylonitrileHCID 11430Potassium CarbonateHCID 10714321HCID 10714321, compound

Product 1

HCID 67618154HCID 67618154, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(-)-(3S,4R)-6-Cyano-3,4-dihydro-4-[(1,6-dihydro-6-oxo-3-pyridazinyl)amino]-2,2-bis(methoxymethyl)-2H-1-benzopyran-3-ol (150 mg, 0.40 mmol) obtained in Example 8 and acrylonitrile (0.055 ml, 0.806 mmol) were dissolved in dimethylformamide (3 ml). Potassium carbonate (111 mg) was added and the mixture was reacted at 50° C. overnight. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (methanol:chloroform=1:30) to give 99 mg of the title compound (58%).

Workup

  1. customthe mixture was reacted at 50° C. overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methanol:chloroform=1:30)

Sources & evidence

ORD record
ord-a0d21df0056f48d8b3efbc0b9294fab5
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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