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

HRID 2279291ノート

反応式

HRID 2279291 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 667473966-Methoxy-1,5-naphthyridin-3-amine収率 21.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2554ed99bbee4144b88c4af77bcd6b26
出典データセット
uspto-grants-2015_09
特許番号
US09133219B2

反応ノート

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