HCID 86732227, compound → HCID 86732228, compound

HRID 930395Notes

Reaction equation

HRID 930395 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[C@:12]1([CH2:23][F:24])[CH2:17][C@@H:16]([C:18]([F:21])([F:20])[F:19])[O:15][C:14]([NH2:22])=[N:13]1>CCO.[Pd]>[NH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([F:1])=[C:3]([C@:12]2([CH2:23][F:24])[CH2:17][C@@H:16]([C:18]([F:21])([F:19])[F:20])[O:15][C:14]([NH2:22])=[N:13]2)[CH:4]=1

Participants

4

Reactant 1

HCID 86732227HCID 86732227, compound

Product 1

HCID 86732228HCID 86732228, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (4S,6S)-4-(2,3-difluoro-5-nitrophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (1.85 g, 5.18 mmol) and palladium 10 wt. % (dry basis) on activated carbon, wet (1.000 mL, 0.940 mmol) in EtOH (20 mL) was hydrogenated under a hydrogen balloon for 4 days until full conversion to the desired product. The reaction mixture was filtered through celite and the filter cake was rinsed with EtOAc followed by MeOH/DCM (10%). The filtrate was concentrated to dryness. The residue was triturated with DCM and the resulted suspension was filtered through filter paper. The filter cake was washed with DCM and dried in air to afford (4S,6S)-4-(5-amino-2,3-difluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (1.2 g, 3.67 mmol, 70.8% yield) as off-white solid. MS m/z=328.1 [M+H]+. Calculated for C12H11F6N30: 327.2

Workup

  1. customfor 4 days

Sources & evidence

ORD record
ord-00599ad4ea8d4d86984c4c8a1159300e
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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