Selenium Dioxide → HCID 59722730, compound

HRID 1664845Notes

Reaction equation

HRID 1664845 reaction equation
[Se](=O)=[O:2].[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:12]1[CH2:18][N:17]2[C:19]([CH3:22])=[CH:20][N:21]=[C:16]2[C@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:14][CH2:13]1>O1CCOCC1>[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:12]1[CH2:18][N:17]2[C:19]([CH:22]=[O:2])=[CH:20][N:21]=[C:16]2[C@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 86620131HCID 86620131, compound

Product 1

HCID 59722730HCID 59722730, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Selenium dioxide (1.73 g, 15.63 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-methyl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (2.95 g, 7.82 mmol) in dioxane (200 mL) and the mixture heated to reflux. After 8 h, the reaction mixture was filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→40% ethyl acetate/dichloromethane) gave the title compound (2.56 g). MS 392.2 (M+1). 1H NMR (500 MHz, CDCl3) δ 9.69 (s, 1H), 7.68 (s, 1H), 7.13-7.06 (m, 2H), 6.96-6.93 (m, 1H), 6.26 (d, J=6.1 Hz, 1H), 5.56 (d, J=14.2 Hz, 1H), 4.91 (dd, J=9.8, 6.6 Hz, 1H), 4.13-4.08 (m, 1H), 3.02 (t, J=11.2 Hz, 1H), 2.43 (d, J=13.4 Hz, 1H), 2.28 (dd, J=24.5, 12.1 Hz, 1H), 2.18-1.16 (m, 1H), 1.50 (s, 9H).

Workup

  1. temperaturethe mixture heated to reflux
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (100% dichloromethane→40% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-f0eb91ae78224d5da1b41c6c536016c3
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

Loading…