Pyridine → HCID 23121896, compound

HRID 1713540Notes

Reaction equation

HRID 1713540 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[F:29][C:30]1[CH:35]=[CH:34][C:33](/[CH:36]=[CH:37]/[S:38](Cl)(=[O:40])=[O:39])=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[F:29][C:30]1[CH:31]=[CH:32][C:33](/[CH:36]=[CH:37]/[S:38]([N:13]2[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:11]3[CH2:12]2)(=[O:40])=[O:39])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12114475315495-38-6HCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121896HCID 23121896, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (50 mg, 0.17 mmol) in chloroform (2 mL) were sequentially added pyridine (0.5 mL) and (E)-2-(4-fluorophenyl)vinylsulfonyl chloride (43 mg, 0.24 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) and crystallized from diisopropyl ether to obtain the title compound (27 mg, yield 64%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)
  3. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3ba1a5a77d8d4d2c83b84002301cea83
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

Loading…