2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 11312463, compound

HRID 272427Notes

Reaction equation

HRID 272427 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([F:18])[C:7]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:27])C=CC=CC=1>ClCCl>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:16]([CH3:17])=[O:27])[N:14]=[CH:15][C:10]=3[CH:9]=[C:8]([F:18])[C:7]2=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 223298828-Cyclopentyl-6-fluoro-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 11312463HCID 11312463, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Cyclopentyl-6-fluoro-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (10.5 g, 37.9 mmol) and 2-benzenesulfonyl-3-phenyl-oxaziridine (11.8 g, 45.4 mmol) were combined in dichloromethane (120 ml) and stirred at room temperature for 18 hours. The mixture was evaporated to an oil, crystallized from ethyl acetate/diethyl ether, filtered and dried in vacuo to provide 8-cyclopentyl-6-fluoro-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one as a white solid (8.88 g, 79.6%). 1H NMR δ (400 MHz, CDCl3) 8.94 (s, 1H), 7.25 (d, 1H), 6.06-5.99 (m, 1H), 2.98 (s, 3H), 2.28-2.21 (m, 2H), 2.18-2.12 (m, 2H), 2.02-1.94 (m, 2H), 1.74-1.67 (m, 2H).

Workup

  1. customThe mixture was evaporated to an oil
  2. customcrystallized from ethyl acetate/diethyl ether
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b40dbda0cf9b4ed582438e5ee2296aec
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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