2(1H)-Quinoxalinone, 3,4-dihydro- → HCID 57809796, compound

HRID 2105991Notes

Reaction equation

HRID 2105991 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[CH3:21][N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH2:24][C:23]1=[O:32].N1C2C(=CC=CC=2)NCC1=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:22]([CH3:21])[C:23](=[O:32])[CH2:24]2)[CH:7]=1

Participants

6

Reactant 4

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-HCID 516892Sodium BicarbonateHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxiraneHCID 212971951-Methyl-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 57809796HCID 57809796, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (98.8 mg) and 1-methyl-3,4-dihydro-1H-quinoxalin-2-one (prepared as the minor regioisomer following a similar procedure described for 3,4-dihydro-1H-quinoxalin-2-one; R. E. TenBrink et al., J. Med. Chem., 1994, 37, pp. 758-768) (165 mg) in dimethylformamide (0.75 mL) was heated at 140° C. for 60 hours. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution and extracted twice with diethyl ether. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 20% ethyl acetate-hexanes) to give the title compound as a pale yellow solid (16.2 mg), m.p. 132° C.-134° C.

Workup

  1. extractionextracted twice with diethyl ether
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography with silica gel (eluted with 20% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-348698a6604242b99ff719ef81360c23
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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