5-Methoxy-3-pyridinecarboxaldehyde → HCID 68053719, 화합물

HRID 1048938노트

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HRID 1048938 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=O)[CH:6]=[N:7][CH:8]=1.[F:11][C:12]1[CH:13]=[C:14]([NH:19][CH3:20])[C:15]([NH2:18])=[CH:16][CH:17]=1>CN(C=O)C.O.C(OCC)(=O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]2[N:18]=[C:9]([C:5]3[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:19]([CH3:20])[C:14]=2[CH:13]=1

참가 물질

6

반응물 2

HCID 109755495-Methoxy-3-pyridinecarboxaldehydeHCID 184572835-Fluoro-N1-methylbenzene-1,2-diamine

생성물 1

HCID 68053719HCID 68053719, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

To a solution of 5-methoxypyridine-3-carbaldehyde (0.052 g, 0.378 mmol) in DMF (1.89 mL) were added the title compound from Example 1 Step B (0.053 g, 0.38 mmol) and Na2S2O5 (0.288 g, 1.51 mmol). The resulting mixture was stirred at 120° C. overnight, then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: LCMS m/z 258.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.56 (d, J=1.6 Hz, 1 H), 8.46 (d, J=2.9 Hz, 1 H), 7.66 (dd, J=8.6, 4.8 Hz, 1 H), 7.65 (t, J=2.1, 2.1 Hz, 1 H), 7.12-7.06 (m, 2 H), 3.95 (s, 3 H), 3.88 (s, 3 H).

후처리

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-f72b5d97ba9245de8e13dbd2f23445c0
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382226B2

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