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

HRID 2105991
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HRID 2105991 반응식
[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
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참가 물질

6

반응물 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

생성물 1

HCID 57809796HCID 57809796, 화합물

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-348698a6604242b99ff719ef81360c23
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07579469B2

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