Ethyl Acetate → 4-[(3-Chloro-4-methoxybenzyl)amino]-1-(2-oxo-7-azaspiro[3.5]non-7-yl)-6-phthalazine carbonitrile

HRID 2300180Notes

Reaction equation

HRID 2300180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([N:19]2[CH2:28][CH2:27][C:22]3([CH2:25][CH:24]([OH:26])[CH2:23]3)[CH2:21][CH2:20]2)=[N:9][N:8]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]([N:19]2[CH2:28][CH2:27][C:22]3([CH2:25][C:24](=[O:26])[CH2:23]3)[CH2:21][CH2:20]2)=[N:9][N:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 9804461HCID 9804461, compound

Product 1

HCID 98905224-[(3-Chloro-4-methoxybenzyl)amino]-1-(2-oxo-7-azaspiro[3.5]non-7-yl)-6-phthalazine carbonitrileYield 84.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 mg of 4-[(3-chloro-4-methoxybenzyl)amino]-1-(2-hydroxy-7-azaspiro[3.5]non-7-yl)-6-phthalazine carbonitrile was suspended in 20 ml dichloromethane and 10 ml tetrahydrofuran, then 690 mg of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxsol-3(1H)-one was added thereto, and the mixture was stirred at room temperature for 15 min. Ethyl acetate, 30 ml saturated aqueous sodium bicarbonate and 2 ml saturated aqueous sodium thiosulfate 5H2O were added thereto. The organic layer was recovered and the aqueous layer was extracted with ethyl acetate. The extracted solutions were combined, washed with brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated and the resulting residue was purified by silica gel column chromatography, crystallized from ethanol, and the resulting crystals were collected filtration by adding hexane thereto to give 420 mg of 4-[(3-chloro-4-methoxybenzyl)amino]-1-(2-oxo-7-azaspiro[3.5]non-7-yl)-6-phthalazine carbonitrile.

Workup

  1. customThe organic layer was recovered
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography
  8. customcrystallized from ethanol
  9. customthe resulting crystals were collected
  10. filtrationfiltration
  11. additionby adding hexane

Sources & evidence

ORD record
ord-d21d73828d0e4017aadfe1f654876c57
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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