2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 88879943, compound

HRID 407190Notes

Reaction equation

HRID 407190 reaction equation
[C:1]([C:3]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([C:21]([NH:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]3[S:30][CH3:31])=[O:22])[C:13](=[O:20])[N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH2:5][CH2:4]1)#[N:2].C1(C2[O:46]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>ClCCl>[C:1]([C:3]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([C:21]([NH:23][C@@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]3[S@:30]([CH3:31])=[O:46])=[O:22])[C:13](=[O:20])[N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 88879942HCID 88879942, compound

Product 1

HCID 88879943HCID 88879943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-1-[(4-cyano-4-pyridin-2-ylpiperidin-1-yl)methyl]-N-[(1R,2R)-2-(methylthio)cyclohexyl]-4-oxo-4H-quinolizine-3-carboxamide (Example 16, 0.035 g, 0.067 mmol) in 2 mL of dichloromethane at 0° C. was added 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (Davis reagent, 0.019 g, 0.074 mmol). After 45 min, the mixture was washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-5% methanol in dichloromethane to provide the title compound that gave a proton NMR spectra consistent with theory and a high resolution mass spectrum (ES+) m/z of 532.2390 calculated for M+H+ [C29H34N5O3S: 532.2377]: 1H NMR (400 MHz, CDCl3) δ 10.02-9.99 (m, 1H), 9.42-9.40 (m, 1H), 8.66 (s, 1H), 8.60-8.57 (m, 1H), 8.22-8.19 (m, 1H); 7.76-7.67 (m, 2H), 7.62-7.60, 7.32-7.21 (m, 1H), 4.29-4.26 (m, 1H), 4.13-4.03 (m, 1H), 3.81 (s, 2H), 3.01-2.83 (m, 2H), 2.82-2.78 (m, 1H), 2.61 (s, 3H), 2.47-2.43 (m, 1H), 2.32-2.26 (m, 2H), 2.14-2.06 (m, 4H), 2.05-1.84 (m, 2H), 1.83-1.36 (m, 2H).

Workup

  1. washthe mixture was washed 3× with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-1c3d15da12d441c29c1cf5d649f96c1f
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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