Dimethyl Sulfoxide → Methyl 6-(((5-methyl-3-phenylisoxazol-4-yl)methyl)amino)nicotinate

HRID 83288

반응식

HRID 83288 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1NC.Cl[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1.[CH:26]([N:29](CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([NH:29][CH2:26][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:17][CH:18]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 59594513(5-Methyl-3-phenyl-4-isoxazolyl)-methylamine

생성물 1

HCID 68443539Methyl 6-(((5-methyl-3-phenylisoxazol-4-yl)methyl)amino)nicotinate수율 46.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
160 °C

실험 절차

A mixture of (5-methyl-3-phenyl-4-isoxazolyl)-methylamine (200 mg, 1.06 mmol), methyl 6-chloronicotinate (182 mg, 1.06 mmol), N,N-diisopropyl ethyl amine (364 μL, 2.13 mmol) and DMSO (2 mL) was heated in the microwave to 160° C. for 0.5 h. It was diluted with ethyl acetate (8 mL) and washed with aqueous sodium carbonate (saturated, 8 mL), water (8 mL) and brine (8 mL). The combined aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (158 mg, 46%) as a light yellow oil. MS: m/e=324.3 [M+H]+.

후처리

  1. washwashed with aqueous sodium carbonate (saturated, 8 mL), water (8 mL) and brine (8 mL)
  2. extractionThe combined aqueous layers were extracted with ethyl acetate (10 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

출처 및 근거

ORD 기록
ord-d6f0e4ff98fb4548b255d2fe6f0dd391
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846719B2

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