Ethanol → (2-Chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamino)-acetic acid ethyl ester

HRID 856980노트

반응식

HRID 856980 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)=[CH:4][C:3]=1[NH2:19].[CH2:20]([OH:22])[CH3:21].C([CH2:25][C:26](OBr)=[O:27])C.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:20]([O:22][C:26](=[O:27])[CH2:25][NH:19][C:3]1[CH:4]=[C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)[CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:21]

참가 물질

6

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 99956372-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamineHCID 23177133Bromo ethylacetate

생성물 1

HCID 16222810(2-Chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamino)-acetic acid ethyl ester수율 94%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a 10 mL microwave reaction flask reaction charged with a magnetic stir bar, was added 2-chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine (0.100 g, 0.320 mmol), anhydrous ethanol (1.3 mL), bromo ethylacetate (0.241 g, 1.44 mmol) and triethylamine (67 μL, 0.48 mmol). The suspension was reacted at 120° C., for 15 min in a microwave set at 70 watts. The resulting yellow suspension was diluted with ethyl acetate (50 mL) and the organic layer was then washed with H2O (2×15 mL), brine (10 mL), dried over MgSO4, and the solvent was removed by evaporation. The white solid was then purified by flash column chromatography (silica gel, elution with EtOAc:hexanes, 1:5) to yield 0.119 g (94%) of the title compound as a white solid. 1H NMR (CDCl3): 7.59 (dd, 1H, J=5.2 and 1.4 Hz), 7.47 (dd, 1H, J=8.3 and 1.7 Hz), 7.38 (dd, 1H, J=8.3 and 1.1 Hz), 7.27 (d, 1H, J=1.7 Hz), 7.10 (dd, 1H, J=5.2 and 1.4 Hz), 5.11 (t, 1H, J=5.0 Hz), 4.29 (q, 2H, J=7.1 Hz), 4.05 (d, 2H, J=5.2 Hz), 1.33 (t, 3H, J=7.1 Hz).

후처리

  1. customTo a 10 mL microwave reaction flask reaction
  2. additioncharged with a magnetic stir bar
  3. customThe suspension was reacted at 120° C., for 15 min in a microwave
  4. washthe organic layer was then washed with H2O (2×15 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed by evaporation
  7. customThe white solid was then purified by flash column chromatography (silica gel, elution with EtOAc:hexanes, 1:5)

출처 및 근거

ORD 기록
ord-39229a8998f944d3a1c196e06ac9272d
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144876B2

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