Butyryl chloride → N-[6-(trifluoromethyl)-1H-indazol-3-yl]butanamide

HRID 497596

反応式

HRID 497596 の反応式
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[F:7][C:8]([F:20])([F:19])[C:9]1[CH:17]=[C:16]2[C:12]([C:13]([NH2:18])=[N:14][NH:15]2)=[CH:11][CH:10]=1>N1C=CC=CC=1>[F:20][C:8]([F:7])([F:19])[C:9]1[CH:17]=[C:16]2[C:12]([C:13]([NH:18][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[N:14][NH:15]2)=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 8855Butyryl chlorideHCID 8179093-Amino-6-(trifluoromethyl)-1H-indazole

生成物 1

HCID 10265187N-[6-(trifluoromethyl)-1H-indazol-3-yl]butanamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

0.26 cm3 of butyryl chloride is added to 500 mg of 6-(trifluoromethyl)-1H-indazole-3-amine, prepared as described in patent U.S. Pat. No. 3,133,081, in 5 cm3 of pyridine, cooled to about 10° C. The temperature is allowed to return to about 19° C. over 19 hours. The reaction medium is evaporated under reduced pressure (2 kPa; 50° C.). The residue is taken up in 15 cm3 of ethyl acetate and 15 cm3 of distilled water. The organic phase is washed with 15 cm3 of distilled water and with 15 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered through a sinter funnel and then evaporated under reduced pressure (2 kPa; 50° C.). The residue is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume) and collecting 20 cm3 fractions. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). After drying (90 Pa; 45° C.), 49 mg of N-[6-(trifluoromethyl)-1H-indazol-3-yl]butanamide are thus obtained in the form of a white solid melting at 200° C.

後処理

  1. customprepared
  2. customThe reaction medium is evaporated under reduced pressure (2 kPa; 50° C.)
  3. washThe organic phase is washed with 15 cm3 of distilled water and with 15 cm3 of saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered through a sinter funnel
  6. customevaporated under reduced pressure (2 kPa; 50° C.)
  7. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  8. washon a column of silica gel (particle size 40-60 μm; diameter 2 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  9. customcollecting 20 cm3 fractions
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. dry with materialAfter drying (90 Pa; 45° C.), 49 mg of N-[6-(trifluoromethyl)-1H-indazol-3-yl]butanamide

出典と根拠

ORDレコード
ord-7a70d606c6554340a7f21adf96f10681
出典データセット
uspto-grants-2005_09
特許番号
US06949579B2

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