Methanol → HCID 86732273, compound

HRID 930436Notes

Reaction equation

HRID 930436 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]1([CH3:28])[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.C1CCN2C(=NCCC2)CC1>CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]1([CH3:28])[CH2:14][C@@H:13]([C:15]([F:18])([F:16])[F:17])[O:12][C:11]([NH2:19])=[N:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86732272HCID 86732272, compound

Product 1

HCID 86732273HCID 86732273, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of N-((4S,6S)-4-(2-chloro-3-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (1.73 g, 4.17 mmol), methanol (25 mL) and DBU (0.798 mL, 5.30 mmol) was stirred at 55° C. overnight. The mixture was concentrated in vacuo, diluted with water and EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude was purified by silica gel chromatography: 0-100% EtOAc-hexane to give (4S,6S)-4-(2-chloro-3-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine as a white solid (1.07 g, 82% yield). MS m/z=415 [M+H]+. Calculated for C19H15ClF4N2O2: 414.8.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with water and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f0f4e551e86a4a0fbf91a25c5f517b6a
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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