Potassium Acetate → HCID 10714321, compound

HRID 862483Notes

Reaction equation

HRID 862483 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[K+].ClC1[N:12]=[N:11][C:10]([NH:13][C@@H:14]2[C:19]3[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:18]=3[O:17][C:16]([CH2:29][O:30][CH3:31])([CH2:26][O:27][CH3:28])[C@H:15]2[OH:32])=[CH:9]C=1>C(O)(=O)C>[C:24]([C:21]1[CH:22]=[CH:23][C:18]2[O:17][C:16]([CH2:26][O:27][CH3:28])([CH2:29][O:30][CH3:31])[C@@H:15]([OH:32])[C@H:14]([NH:13][C:10]3[CH:9]=[CH:2][C:1](=[O:4])[NH:12][N:11]=3)[C:19]=2[CH:20]=1)#[N:25]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 10691833HCID 10691833, compound

Product 1

HCID 10714321HCID 10714321, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium acetate (380 mg) and acetic acid (6 ml) were added to (-)-(3S,4R)-4-[(6-chloro-3-pyridazinyl)amino]-6-cyano-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1benzopyran-3-ol (750 mg) obtained in Example 5, and the mixture was refluxed with stirring for 5 hours. The reaction mixture was filtered and the residue was washed with acetic acid. The residue obtained by removing the solvent from the filtrate under reduced pressure was purified by silica gel column chromatography (ethyl acetate:ethanol=95:5), whereby (-)-(3S,4R)-4-[(6-acetyloxy-3-pyridazinyl)amino]-6-cyano-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1-benzopyran-3-ol (180 mg, 22.6%) and (-)-(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 (500 mg, 69.9%) were obtained in the order of elution.

Workup

  1. temperaturethe mixture was refluxed
  2. filtrationThe reaction mixture was filtered
  3. washthe residue was washed with acetic acid
  4. customThe residue obtained
  5. customby removing the solvent from the filtrate under reduced pressure
  6. customwas purified by silica gel column chromatography (ethyl acetate:ethanol=95:5), whereby (-)-(3S,4R)-4-[(6-acetyloxy-3-pyridazinyl)amino]-6-cyano-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1-benzopyran-3-ol (180 mg, 22.6%)

Sources & evidence

ORD record
ord-cc0fa3c44360418e9b02af345093d728
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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