Water → HCID 11796058, compound

HRID 862484Notes

Reaction equation

HRID 862484 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].Br[CH2:29][CH2:30][CH3:31].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]([CH2:29][CH2:30][CH3:31])[N:21]=3)[C:7]=2[CH:27]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 10714321HCID 10714321, compound

Product 1

HCID 11796058HCID 11796058, compoundYield 50%

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 (60 mg, 0.16 mmol) obtained in Example 8 and 1-bromopropane (0.017 ml, 0.19 mmol) were dissolved in dimethylformamide (1.0 ml). Potassium carbonate (45 mg) was added and the mixture was reacted at 70° C. for 3 hours. 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 to give a residue. The residue was purified by silica gel column chromatography (methanol:chloroform=4:96) to give 33 mg of the title compound (50%).

Workup

  1. customthe mixture was reacted at 70° C. for 3 hours
  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. customto give a residue
  7. customThe residue was purified by silica gel column chromatography (methanol:chloroform=4:96)

Sources & evidence

ORD record
ord-b890c2a1e74745a691d95406812106da
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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