Trifluoroacetic acid → 6-Methoxy-1,5-naphthyridin-3-amine

HRID 2279291노트

반응식

HRID 2279291 반응식
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[N:22][C:21]([O:25][CH3:26])=[CH:20][CH:19]=2)(C)(C)C>ClCCl>[NH2:14][C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[N:22][C:21]([O:25][CH3:26])=[CH:20][CH:19]=2

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 66747191(6-Methoxy-[1,5]naphthyridine-3-yl)-carbamic acid tert-butyl ester

생성물 1

HCID 667473966-Methoxy-1,5-naphthyridin-3-amine수율 21.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (101 mL, 1.32 mol, 20.85 eq) is added to a stirred solution of (6-methoxy-[1,5]naphthyridine-3-yl)-carbamic acid tert-butyl ester (18.2 g, 66.11 mmol, 1.0 eq) in dichloromethane (500 mL). After 19 hours stirring at room temperature, the solution is evaporated to dryness, 6N sodium hydroxide aqueous solution is added to adjust pH to 9˜10 and a lot of solid precipitated. The mixture is extracted with dichloromethane (200 mL) and the residue is extracted with ethyl acetate (3×250 mL). Evaporation of the dichloromethane phase gives 2.44 g of product with 83% purity, which is then purified by column chromatography (silica gel, eluent: dichloromethane:petroleum ether:ethyl acetate, 25:25:2, v/v/v) to afford 6-methoxy-[1,5]naphthyridin-3-ylamino as a light yellow solid (1.95 g with 98% purity). Evaporation of the ethyl acetate phase yields additional 9.88 g of light yellow product with 99% purity. Total: 11.83 g (98% yield).

후처리

  1. customthe solution is evaporated to dryness, 6N sodium hydroxide aqueous solution
  2. additionis added
  3. customa lot of solid precipitated
  4. extractionThe mixture is extracted with dichloromethane (200 mL)
  5. extractionthe residue is extracted with ethyl acetate (3×250 mL)
  6. customEvaporation of the dichloromethane phase

출처 및 근거

ORD 기록
ord-2554ed99bbee4144b88c4af77bcd6b26
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133219B2

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