1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86732240, compound

HRID 930403Notes

Reaction equation

HRID 930403 reaction equation
[F: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.N12CCCN=C1CCCCC2>CO>[F: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

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86732241HCID 86732241, compound

Product 1

HCID 86732240HCID 86732240, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-((4S,6S)-4-(2,3-difluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (7.0 g, 17.57 mmol) in MeOH (100 mL) was added 1,8-diazabicyclo-[5.4.0]undec-7-ene (3.15 mL, 21.09 mmol). The mixture was brought up to 60° C. for 15 h until the conversion was completed. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The separated organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and purified by silica gel column (0-60% EtOAc/hexane) to afford (4S,6S)-4-(2,3-difluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (4.94 g, 16.79 mmol, 96% yield) as white crystalline solid. MS m/z=295.1 [M+H]+. Calculated for C12H11F5N2O: 294.2

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column (0-60% EtOAc/hexane)

Sources & evidence

ORD record
ord-3af649c86ff74360b60a4620f4f01b0d
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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