HCID 71112643, compound → HCID 86712811, compound

HRID 876380Notes

Reaction equation

HRID 876380 reaction equation
[F:1][C:2]1([F:21])[CH2:7][O:6][C:5]([NH2:8])=[N:4][C@:3]1([CH2:19][F:20])[C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[F:18]>C(O)C.[Pd]>[NH2:15][C:13]1[CH:12]=[CH:11][C:10]([F:18])=[C:9]([C@:3]2([CH2:19][F:20])[C:2]([F:21])([F:1])[CH2:7][O:6][C:5]([NH2:8])=[N:4]2)[CH:14]=1

Participants

4

Reactant 1

HCID 71112643HCID 71112643, compound

Product 1

HCID 86712811HCID 86712811, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-5,5-difluoro-4-fluoromethyl-4-(2-fluoro-5-nitro-phenyl)-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate F7.1) (38.2 mg, 120 μmol) in ethanol (2 ml) was hydrogenated at atmospheric pressure using palladium (10% on carbon) (6.4 mg, 6 μmol) as the catalyst during 15 hours at room temperature. The reaction mixture was filtrated over a layer of Dicalite®, which was washed with ethanol (2×10 ml). The combined solutions of ethanol were evaporated at reduced pressure. The (S)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-fluoromethyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (36 mg, quantitative yield) was obtained as a light red solid and was engaged in the following step without further purification. MS (ISP): m/z=278.2 [M+H]+.

Workup

  1. customduring 15 hours
  2. customat room temperature
  3. filtrationThe reaction mixture was filtrated over a layer of Dicalite®, which
  4. washwas washed with ethanol (2×10 ml)
  5. customThe combined solutions of ethanol were evaporated at reduced pressure

Sources & evidence

ORD record
ord-b8ae96ce56314d7abdc4c270e19d2930
Source dataset
uspto-grants-2015_03
Patent number
US08987255B2

Reaction notes

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