Hexane → N-(i-propyl)-4-dimethylamino-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250494노트

반응식

HRID 1250494 반응식
Br[C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:3]=1.CCCCCC.[Li]CCCC.[CH:33]([N:36]=[C:37]=[O:38])([CH3:35])[CH3:34]>C(OCC)C>[CH:33]([NH:36][C:37]([C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:3]=1)=[O:38])([CH3:35])[CH3:34]

참가 물질

6

반응물 4

HCID 8058HexaneHCID 61277Isopropyl isocyanateHCID 212498292-Bromo-N,N-dimethyl-6-[3-(trifluoromethyl)phenoxy]pyridin-4-amineHCID 178418339Butyllithium

생성물 1

HCID 15906607N-(i-propyl)-4-dimethylamino-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

0.75 g (0.0021 mol) of 2-bromo-4-dimethylamino-6-{3-(trifluoromethyl)phenoxy} pyridine was suspended in about 15 ml of diethyl ether. While cooling the obtained suspension in a dry ice-acetone bath in an argon atmosphere, 1.4 ml of a 1.65M-hexane solution of BuLi (0.0021×1.1 mol) was added thereto, followed by stirring the suspension for about 10 minutes. After 0.35 g (0.0021×2.0 mol) of isopropyl isocyanate dissolved in about 10 ml of diethyl ether was added to the reaction solution, the obtained solution was removed from the bath and stirred at room temperature for about one hour. The reaction solution was mixed with about 5 ml of a 1N-hydrochloric acid aqueous solution, and then distributed in ethyl acetate-saturated sodium bicarbonate water, followed by washing with saturated brine. The organic phase of the obtained solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane) and reversed phase column (Lobor LiCHroprep RP-10; eluting solution: acetonitrile/water), thereby obtaining an aimed product.

후처리

  1. additionwas added
  2. additionwas added to the reaction solution
  3. customthe obtained solution was removed from the bath
  4. stirringstirred at room temperature for about one hour
  5. additionThe reaction solution was mixed with about 5 ml of a 1N-hydrochloric acid aqueous solution
  6. washby washing with saturated brine
  7. dry with materialThe organic phase of the obtained solution was dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-c7110a3ab56f45a3a4f2d0bd7f468836
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339045B1

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