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

HRID 598223노트

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HRID 598223 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8720ba681d524d7da46f234fc2801101
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897612B2

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