1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 90389292, compound

HRID 1526540Notes

Reaction equation

[F:1][CH:2]([F:27])[C:3]1([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=2[CH3:26])[CH:9]2[CH:7]([CH2:8]2)[O:6][C:5]([NH:10]C(=O)C2C=CC=CC=2)=[N:4]1.N12CCCN=C1CCCCC2>CO>[F:27][CH:2]([F:1])[C:3]1([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=2[CH3:26])[CH:9]2[CH:7]([CH2:8]2)[O:6][C:5]([NH2:10])=[N:4]1

Participants

Conditions

Temperature: 40 °C

Procedure

N-(5-(difluoromethyl)-5-(3-fluoro-2-methylphenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-yl)benzamide (1.0 g, 2.67 mmol) was dissolved in methanol (50 mL) under nitrogen and 1,8-diazabicyclo-[5.4.0]undec-7-ene (0.798 ml, 5.34 mmol) was added. The reaction was heated to 40° C. After 18 hours, the reaction mixture was concentrated to dryness under reduced pressure and the residue partitioned between water and ethyl acetate. The organic layer was isolated and concentrated under reduced pressure. The crude residue was purified via silica gel flash chromatography eluting with 0-60% ethyl acetate in hexanes afforded the title compound 5-(difluoromethyl)-5-(3-fluoro-2-methylphenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine (0.470 g, 1.739 mmol, 65.1% yield). LC/MS (ESI+) m/z=270.9 (M+H).

Workup

concentrationthe reaction mixture was concentrated to dryness under reduced pressure
customthe residue partitioned between water and ethyl acetate
customThe organic layer was isolated
concentrationconcentrated under reduced pressure
customThe crude residue was purified via silica gel flash chromatography
washeluting with 0-60% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-e1393094838c4e08a93c2dac25e5f685
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085576B2

Reaction notes

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