1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86732207, compound

HRID 930379Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C@:8]2([CH2:27][F:28])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH:18]C(=O)C3C=CC=CC=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.N1CCCN2CCCCCC=12>CO>[Br:1][C:2]1[CH:3]=[C:4]([C@:8]2([CH2:27][F:28])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of N-((4S,6S)-4-(3-bromophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (1.15 g, 2.504 mmol) in MeOH 8 mL was added 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.449 ml, 3.01 mmol) and the resulting mixture was heated at 65° C. for 9 h. The mixture was concentrated, and then diluted with EtOAc. The resulting solution was washed with water, saturated NH4Cl solution, dried over sodium sulfate, filtered, concentrated. The crude material was purified by column chromatographed on silica gel using 0-40% EtOAc/Hexane to give (4S,6S)-4-(3-bromophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (0.480 g, 1.352 mmol, 54.0% yield). MS m/z=356.9 [M+H]+. Calculated for C12H11BrF4NO2: 355.1

Workup

concentrationThe mixture was concentrated
additiondiluted with EtOAc
washThe resulting solution was washed with water, saturated NH4Cl solution
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by column
customchromatographed on silica gel using 0-40% EtOAc/Hexane

Sources & evidence

ORD record: ord-1719a96837864b32aa52027b6b0951fc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296734B2

Reaction notes

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