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

HRID 83288

反応式

HRID 83288 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-d6f0e4ff98fb4548b255d2fe6f0dd391
出典データセット
uspto-grants-2014_09
特許番号
US08846719B2

関連ノート

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