HCID 89500641, compound → HCID 89500570, compound

HRID 925448Notes

Reaction equation

HRID 925448 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[C:19]([N:21]=[N+]=[N-])[CH:18]=[CH:17][C:16]=2[F:24])([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CCO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].[Pd]>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=2[F:24])([CH3:14])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 89500641HCID 89500641, compound

Product 1

HCID 89500570HCID 89500570, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 131709914Lindlars catalystCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of [5-(5-azido-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (2.18 g, 6.24 mmol) in EtOAc:EtOH 1:1 (150 ml) was hydrogenated over 10% Pd/C (0.21 g) and Lindlar catalyst (0.21 g) with 0.1 bar H2 for 4.5 h at rt. The reaction mixture was filtered through celite and concentrated to leave the title compound that was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f83f395cc6cd49a9bb0a728118e34cf3
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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