N-((4S,6S)-4-(2-fluoro-3-methylphenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide → (4S,6S)-4-(2-fluoro-3-methylphenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930421Notes

Reaction equation

HRID 930421 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]1([CH2:28][F:29])[CH2:14][C@@H:13]([C:15]([F:18])([F:17])[F:16])[O:12][C:11]([NH:19]C(=O)C2C=CC=CC=2)=[N:10]1>CO>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]1([CH2:28][F:29])[CH2:14][C@@H:13]([C:15]([F:17])([F:18])[F:16])[O:12][C:11]([NH2:19])=[N:10]1

Participants

3

Reactant 1

HCID 86732261N-((4S,6S)-4-(2-fluoro-3-methylphenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

Product 1

HCID 86732260(4S,6S)-4-(2-fluoro-3-methylphenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amineYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-((4S,6S)-4-(2-fluoro-3-methylphenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (1.69 g, 4.10 mmol) in MeOH (20 mL) was added dbu (0.741 ml, 4.92 mmol) and the resulting mixture was heated at 50° C. for 17 h. The reaction went to completion. The mixture was concentrated and chromatographed on silica gel using 0-30% EtOAc/hexanes to afford a white foam as (4S,6S)-4-(2-fluoro-3-methylphenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (1.13 g, 3.67 mmol, 89% yield). MS m/z=308.9 [M+H]+. Calculated for C13H13F5N2O: 308.09.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed on silica gel using 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-fc0c4ca367294d71b8b977d1ac86a819
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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