HCID 86724986, compound → HCID 86724985, compound

HRID 1847059Notes

Reaction equation

HRID 1847059 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=3[N:19]=2)[C:7](=[O:21])[CH2:6]1)=[N+]=[N-]>CO.O1CCCC1.[Pd]>[NH2:1][CH2:4][C@H:5]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=3[N:19]=2)[C:7](=[O:21])[CH2:6]1

Participants

4

Reactant 1

HCID 86724986HCID 86724986, compound

Product 1

HCID 86724985HCID 86724985, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 6-[(4R)-4-(azidomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (230 mg, 0.877 mmol) in methanol-tetrahydrofuran (5 ml-2.5 ml) was added 10% palladium on carbon catalyst (about 50% aqueous, 130 mg) at room temperature and the mixture was stirred at the same temperature for 2 hours under a hydrogen atmosphere. The catalyst was removed by filtration and washed with methanol, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After removing the drying agent by filtration, the filtrate was concentrated under reduced pressure so as to yield 188 mg (90%) of the title compound in the form of a colorless solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removing the drying agent
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated under reduced pressure so as

Sources & evidence

ORD record
ord-11e2abc30d5145cda6c841907a6585c6
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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