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Water → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1698080
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HRID 1698080 반응식
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH3:19][NH2:20].O.ClCCl>C(O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:10]2[S:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:20][CH3:19])=[N:7][CH:6]=3)=[N:12][C:11]=2[CH:13]=1
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6

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HCID 962WaterHCID 6329MethylamineHCID 6344DichloromethaneHCID 575534102-(6-Fluoropyridin-3-yl)-5-methoxy-1,3-benzothiazole

생성물 1

HCID 248037275-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
100 °C

실험 절차

To 2-(6-fluoropyridin-3-yl)-5-methoxy-1,3-benzothiazole (59.2 mg, 0.227 mmol) was added methylamine in ethanol (8 M, 2 mL) and the reaction mixture was heated in a microwave oven at 100° C. for 5 min. Water and dichloromethane were added and the layers separated. The aqueous phase was extracted with dichloromethane (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and the solvent removed in vacuo. The crude material was purified by column chromatography (heptane/EtOAc 60:40 to 50:50) to give the title compound (39 mg) as a pale yellow solid. 1H NMR δ ppm 8.68 (d, 1H) 7.98 (dd, 1H) 7.91 (d, 1H) 7.50 (d, 1H) 7.27 (q, 1H) 7.01 (dd, 1H) 6.59 (d, 1H) 3.85 (s, 3H) 2.86 (d, 3H); MS m/z (M+H) 272.

후처리

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted with dichloromethane (3×)
  3. washThe combined organic phases were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe crude material was purified by column chromatography (heptane/EtOAc 60:40 to 50:50)

출처 및 근거

ORD 기록
ord-6b7d955fc8b44642b5a525abd75766a2
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163928B2

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