HCID 90389371, compound → HCID 90389399, compound

HRID 1526542Notes

Reaction equation

HRID 1526542 reaction equation
[F:1][CH:2]([F:22])[C:3]1([C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[C:13]([F:20])[C:12]=2[CH3:21])[CH:9]2[CH:7]([CH2:8]2)[O:6][C:5]([NH2:10])=[N:4]1>C1COCC1.[Pd]>[NH2:17][C:15]1[CH:14]=[C:13]([F:20])[C:12]([CH3:21])=[C:11]([C:3]2([CH:2]([F:1])[F:22])[CH:9]3[CH:7]([CH2:8]3)[O:6][C:5]([NH2:10])=[N:4]2)[CH:16]=1

Participants

4

Reactant 1

HCID 90389371HCID 90389371, compound

Product 1

HCID 90389399HCID 90389399, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
18 °C

Procedure

5-(Difluoromethyl)-5-(3-fluoro-2-methyl-5-nitrophenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine (200 mg, 0.634 mmol) was dissolved in THF (20 ml). 10% palladium on carbon (135 mg, 0.127 mmol) was added and the reaction mixture was put under a balloon of H2 and stirred at 18° C. for 4 h. The mixture was filtered through a pad of celite, washing well with ethyl acetate. The filtrate was concentrated under vacuum to yield crude 5-(5-amino-3-fluoro-2-methylphenyl)-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine (140 mg, 0.491 mmol, 77% yield) as a gray foam. LC/MS (ESI+) m/z=286.2 (M+H)

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing well with ethyl acetate
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-32bff2f7a1234f10ab184de4926d12bf
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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