Sulfuric Acid → 2-((4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)phenoxy)methyl)quinoline

HRID 33824

반응식

HRID 33824 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[N:10][NH:9][C:8]=2[C:12]2[CH:29]=[CH:28][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.[CH3:30]NN.S(=O)(=O)(O)O>C(O)C>[CH3:30][N:10]1[CH:11]=[C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:28][CH:29]=2)=[N:9]1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 6061MethylhydrazineHCID 116105532-((4-(4-pyridin-4-yl-1H-pyrazol-3-yl)phenoxy)methyl)quinoline

생성물 1

HCID 115819362-((4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)phenoxy)methyl)quinoline수율 56%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-[-4-(4-Pyridin-4-yl-2H-pyrazol-3-yl)-phenoxymethyl}-quinoline (1.72 g) in ethanol (20 ml) was added methyl hydrazine (3.5 ml, 1.5 eq.) and concentrated sulfuric acid (0.1 ml). The reaction mixture was stirred 1 h at ambient temperature and solvent evaporated. The reaction mixture was partitioned between methylene chloride and saturated sodium bicarbonate. The layers were separated and the organic layer dried magnesium sulfate, filtered and concentrated. Preparative HPLC chromatography provided the title compound (major isomer) as a clear oil (0.97 g, 56%). 1H NMR (400 MHz, CDCl3) δ 8.44 (d, J=5.0 Hz, 2 H), 8.17 (d, J=8.7 Hz, 1 H), 8.05 (d, J=8.3 Hz, 1H), 7.81 (d, J=7.9 Hz, 1 H), 7.70 (m, 1 H), 7.66 (d, J=8.7 Hz, 1H), 7.54 (s, 1H), 7.53 (m, 1H), 7.37 (d, J=8.7 Hz, 2H) 7.15 (d, J=5.0, 2H), 7.00 (d, J=8.7 Hz, 2H), 5.38 (s, 2H), 3.93 (s, 3H); MS: (M+H m/z=393.3).

후처리

  1. customsolvent evaporated
  2. customThe reaction mixture was partitioned between methylene chloride and saturated sodium bicarbonate
  3. customThe layers were separated
  4. filtrationthe organic layer dried magnesium sulfate, filtered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b0f4146c93ee4ef88310ed6cdf4179d9
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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