Methyl iodide → 8-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445536

반응식

HRID 445536 반응식
[OH-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[NH:14][C:15](=[O:24])[N:16]([C:17]4[C:18]([CH3:23])=[N:19][N:20]([CH3:22])[CH:21]=4)[C:7]=3[C:6]=2[CH:5]=1.I[CH3:26]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[CH:9][C:8]3[N:14]([CH3:26])[C:15](=[O:24])[N:16]([C:17]4[C:18]([CH3:23])=[N:19][N:20]([CH3:22])[CH:21]=4)[C:7]=3[C:6]=2[CH:5]=1

참가 물질

7

반응물 3

HCID 6328Methyl iodide2회HCID 14798Sodium HydroxideHCID 596198918-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

생성물 1

HCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

NaOH (0.568 g, 14.19 mmol) and tetrabutylammonium bromide (0.229 g, 0.710 mmol) were added to a mixture of 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Stage A.1, 3.10 g, 7.100 mmol) in DCM (108 ml) and H2O (54 ml) and stirred at rt for 5 min. Then iodomethane (1.52 ml, 24.1 mmol) was added and the mixture was stirred for 14 h at rt. Iodomethane (0.4 ml, 6.35 mmol) was added and the RM was stirred at rt for 23.5 h. Then the RM was extracted with DCM (2×), washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was dissolved in DCM and purified by flash chromatography (DCM/MeOH 0%-4.5%) to give the title compound as a brownish solid (HPLC: tR 2.37 min (Method A); M+H=374 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.00 (s, 1H), 8.08 (s, 1H), 7.91-7.99 (m, 1H), 7.64-7.71 (m, 1H), 7.41-7.47 (m, 1H), 3.90 (s, 3H), 3.55 (s, 3H), 1.94 (s, 3H))

후처리

  1. stirringthe mixture was stirred for 14 h at rt
  2. stirringthe RM was stirred at rt for 23.5 h
  3. extractionThen the RM was extracted with DCM (2×)
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in DCM
  9. custompurified by flash chromatography (DCM/MeOH 0%-4.5%)

출처 및 근거

ORD 기록
ord-e76b909bf85349afb60cae6ab88cb06e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476294B2

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