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

反応式

HRID 445536 の反応式
[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

参加物

7

反応物 3

HCID 6328Methyl iodide2 回HCID 14798Sodium HydroxideHCID 596198918-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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))

後処理

  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%)

出典と根拠

ORDレコード
ord-e76b909bf85349afb60cae6ab88cb06e
出典データセット
uspto-grants-2013_07
特許番号
US08476294B2

関連ノート

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