HCID 68089343, compound → HCID 68089393, compound

HRID 1772046Notes

Reaction equation

HRID 1772046 reaction equation
C([NH:8][C:9]1[C:14]2[O:15][CH2:16][CH2:17][N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13]=2[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>CO.[Pd]>[NH2:8][C:9]1[C:14]2[O:15][CH2:16][CH2:17][N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13]=2[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 1

HCID 68089343HCID 68089343, compound

Product 1

HCID 68089393HCID 68089393, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of tert-butyl 5-(benzylamino)-2,3-dihydropyrido[3,4-b][1,4]oxazine-1-carboxylate (3.6 g, 10.56 mmol) and 10% Pd on carbon (1.12 g, 1.06 mmol) in MeOH (100 mL) was stirred under hydrogen atmosphere (2 L) at 35° C. for 48 h. The mixture was then filtered through Celite and washed with MeOH (3×25 mL). The combined organic layer was concentrated under reduced pressure. The residue was re-dissolved in EtOAc (100 mL) and washed with brine (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by reverse phase column chromatography (eluting with 22% acetonitrile in water, with 0.1% NH3H2O) to give tert-butyl 5-amino-2,3-dihydropyrido[3,4-b][1,4]oxazine-1-carboxylate (2.1 g, 79% yield) as a yellow solid. ESI MS: m/z 252 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washwashed with MeOH (3×25 mL)
  3. concentrationThe combined organic layer was concentrated under reduced pressure
  4. dissolutionThe residue was re-dissolved in EtOAc (100 mL)
  5. washwashed with brine (2×50 mL)
  6. dry with materialThe combined organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe residue was purified by reverse phase column chromatography (eluting with 22% acetonitrile in water, with 0.1% NH3H2O)

Sources & evidence

ORD record
ord-8e5ffdb6c2d94083804d94043934d2d1
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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