2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 86695068, compound

HRID 574343Notes

Reaction equation

HRID 574343 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:16]=[C:12]3[N:11]=[C:10]([CH3:23])[C:9]=2[CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C2[O:48]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:29])[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[N:14]=[C:15]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:16]=[C:12]3[N:11]=[C:10]([CH3:23])[C:9]=2[CH:24]([OH:48])[C:25]([O:27][CH3:28])=[O:26])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86695066HCID 86695066, compound

Product 1

HCID 86695068HCID 86695068, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of methyl 2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate (106 mg, 0.269 mmol) in anhydrous THF (5 ml) at −78° C. was added dropwise KHMDS (0.808 mL, 0.404 mmol) in toluene. Reaction mixture was stirred at −78° C. for 30 min and to this was added dropwise 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (106 mg, 0.404 mmol) in THF (2 mL) and the contents were stirred at −78° C. for 30 min and allowed slowly to warm to room temperature, then quenched with a drop of saturated ammonium chloride solution. Evaporated to remove the solvent. Purified by prep HPLC to afford methyl 2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (56 mg, 0.134 mmol, 49.8% yield) as white solid. 1H-NMR (500 MHz, CDCl3) δ 1.15 (6 H, s), 1.69-1.75 (4 H, m), 2.62 (3 H, s), 3.77-3.79 (2 H, m), 3.81-3.83 (2 H, m), 3.85 (3 H, s), 5.49 (1 H, s), 7.56-7.60 (3 H, m), 8.20-8.22 (2 H, m).

Workup

  1. customReaction mixture
  2. stirringthe contents were stirred at −78° C. for 30 min
  3. temperatureto warm to room temperature
  4. customquenched with a drop of saturated ammonium chloride solution
  5. customEvaporated
  6. customto remove the solvent
  7. customPurified by prep HPLC

Sources & evidence

ORD record
ord-fee34d6e7cf547e6978efd46263433c0
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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