3,3-Dimethylbutylamine → Ethyl 2-chloro-4-[(3,3-dimethylbutyl)amino]-6-methyl-3-pyridinecarboxylate

HRID 598223ノート

反応式

HRID 598223 の反応式
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([CH3:14])[N:3]=1.[CH3:15][C:16]([CH3:21])([CH3:20])[CH2:17][CH2:18][NH2:19]>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([NH:19][CH2:18][CH2:17][C:16]([CH3:21])([CH3:20])[CH3:15])[CH:5]=[C:4]([CH3:14])[N:3]=1

参加物

5

反応物 2

HCID 197093,3-DimethylbutylamineHCID 604813Ethyl 2,4-dichloro-6-methylnicotinate

生成物 1

HCID 86614972Ethyl 2-chloro-4-[(3,3-dimethylbutyl)amino]-6-methyl-3-pyridinecarboxylate収率 80%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of ethyl 2,4-dichloro-6-methyl-3-pyridinecarboxylate (1.00 g, 4.27 mmol) in ethanol (20.0 mL) was treated with (3,3-dimethylbutyl)amine (0.570 mL, 4.27 mmol). The mixture was refluxed for 2 days, and upon cooling, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The aqueous layer was extracted twice with ethyl acetate. The combined organic portions were dried over magnesium sulfate, filtered, concentrated in vacuo, and purified via flash column chromatography (20-60% ethyl acetate in hexanes) to afford the title compound as an amber oil (1.02 g, 80%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 6.94 (t, J=4.4 Hz, 1H), 6.18 (s, 1H), 4.23 (q, J=7.2 Hz, 2H), 2.82-3.17 (m, 2H), 2.25 (s, 3H), 1.35-1.54 (m, 2H), 1.25 (t, J=7.1 Hz, 3H), 0.84 (s, 9H). MS(ES+) m/e 299 [M+H]+.

後処理

  1. temperatureThe mixture was refluxed for 2 days
  2. temperatureupon cooling
  3. washwashed with saturated aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic portions were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified via flash column chromatography (20-60% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8720ba681d524d7da46f234fc2801101
出典データセット
uspto-grants-2011_03
特許番号
US07897612B2

反応ノート

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