1,2,3,4-Tetrahydroquinoxaline → HCID 57809838, compound

HRID 2105983Notes

Reaction equation

HRID 2105983 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.[NH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH2:23][CH2:22]1>CN(C=O)C.C(OCC)C>[N:21]1([CH2:12][C:10]([OH:11])([CH2:9][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:19][CH3:20])([CH3:18])[CH3:17])[C:13]([F:16])([F:15])[F:14])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 770281,2,3,4-TetrahydroquinoxalineHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 57809838HCID 57809838, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (see Example 1) (54.4 mg) and tetrahydroquinoxaline (124.8 mg) in DMF (0.6 mL) was heated at 100° C. for 6 hours. The resulting mixture was diluted with diethyl ether, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 25% diethyl ether-benzene) to give the title compound as a clear oil (31.2 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (eluted with 25% diethyl ether-benzene)

Sources & evidence

ORD record
ord-b3f905d6a75f40cb9470a8375ad21067
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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