Methylhydrazine → 3-ethyl-2-methoxy-6-methyl-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-pyridine

HRID 1921359ノート

反応式

HRID 1921359 の反応式
C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([O:15][CH3:16])=[N:9][C:8]=1[CH3:17])C.[CH3:19][NH:20]N>C(O)(=O)C>[CH2:13]([C:11]1[C:10]([O:15][CH3:16])=[N:9][C:8]([CH3:17])=[C:7]([C:6]2[N:20]([CH3:19])[N:2]=[CH:4][N:5]=2)[CH:12]=1)[CH3:14]

参加物

4

反応物 2

HCID 6061MethylhydrazineHCID 67492560N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methylnicotinamide

生成物 1

HCID 674922943-ethyl-2-methoxy-6-methyl-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-pyridine収率 61%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

In a round bottom flask under a nitrogen atmosphere N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methyl-nicotinamide (synthesized on 0.567 mmol scale) of Step 2, Example 16 is treated with glacial acetic acid (1 mL) followed by methylhydrazine (50 μL, 0.94 mmol). The resulting mixture is stirred at 90° C. for 12 hr. The reaction mixture is evaporated to dryness and the residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1). Fractions containing the product are combined, evaporated and re-purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (99:1). Fractions containing the product are combined and the solvent evaporated to give 3-ethyl-2-methoxy-6-methyl-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-pyridine (80 mg, 61% yield) as a light yellow oil. MS: m/e=233 (M+H); 1H NMR (δ, ppm): 7.96 (1H, s), 7.29 (1H, s), 3.99 (3H, s), 3.74 (3H, s), 2.59 (2H, q), 2.30 (3H, s), 1.19 (3H, t).

後処理

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1)
  3. additionFractions containing the product
  4. customevaporated
  5. customre-purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (99:1)
  6. additionFractions containing the product
  7. customthe solvent evaporated

出典と根拠

ORDレコード
ord-e0aff15e39114012b72b38ca06be45e8
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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