Lawesson's reagent → HCID 18416160, compound

HRID 990938Notes

Reaction equation

HRID 990938 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[CH:11]=[C:10]3[N:19]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:20](=O)[CH2:21][O:22][C:9]3=[CH:8][C:7]=2[N:6]=1)([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>C1(C)C=CC=CC=1>[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[CH:11]=[C:10]3[N:19]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:20](=[S:38])[CH2:21][O:22][C:9]3=[CH:8][C:7]=2[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 184161447-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-one

Product 1

HCID 18416160HCID 18416160, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-one (EXAMPLE 22) (48.4 mg, 0.119 mmol) and Lawesson's reagent (0.144 g, 0.356 mmol) in 2.4 mL toluene was heated at reflux for 6 h, whereupon the mixture was partitioned between EtOAc (40 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (20 mL), and the combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc) afforded 41 mg of 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-thione, a yellow oil. Data for 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2 (3H)-thione: Rf 0.36 (9:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.72 (broad s, 1H), 7.48 (s, 1H), 7.13 (s, 1H), 5.54 (hept, 1H, J=6.2), 5.32-5.42 (m, 2H), 5.05 (s, 2H), 1.41 (d, 6H, J=6.2).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h, whereupon the mixture
  3. customwas partitioned between EtOAc (40 mL) and water (20 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (20 mL)
  5. washthe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-de7b11697e75414c90bd5fb58fed77ef
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

Loading…