Butyryl chloride → N-(6,7-difluoro-1H-indazol-3-yl)butanamide

HRID 497619ノート

反応式

HRID 497619 の反応式
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[F:7][C:8]1[C:16]([F:17])=[C:15]2[C:11]([C:12]([NH2:18])=[N:13][NH:14]2)=[CH:10][CH:9]=1>N1C=CC=CC=1>[F:7][C:8]1[C:16]([F:17])=[C:15]2[C:11]([C:12]([NH:18][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[N:13][NH:14]2)=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 8855Butyryl chlorideHCID 103972023-Amino-6,7-difluoro-1H-indazole

生成物 1

HCID 11776377N-(6,7-difluoro-1H-indazol-3-yl)butanamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
3 °C

実験手順

0.61 cm3 of butyryl chloride is added to 1 g of 6,7-difluoro-1H-indazole-3-amine, described previously, in 15 cm3 of pyridine, after cooling to about 3° C., and the mixture is then left at room temperature for 76 hours. The reaction medium is concentrated under reduced pressure (2 kPa; 40° C.) and the residue is taken up in 25 cm3 of ethyl acetate and 25 cm3 of water. The organic phase is washed with 25 cm3 of distilled water and then with 25 cm3 of saturated aqueous sodium chloride solution. After drying over magnesium sulphate, filtration and concentration under reduced pressure (2 kPa; 40° C.), the residue obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 3 cm), eluting with a dichloromethane/methanol mixture (98/2 by volume). The fractions containing the expected product are combined and then evaporated under reduced pressure (2 kPa; 40° C.); after drying (90 Pa; 40° C.), 596 mg of N-(6,7-difluoro-1H-indazol-3-yl)butanamide are obtained in the form of a white solid melting at 191° C.

後処理

  1. concentrationThe reaction medium is concentrated under reduced pressure (2 kPa; 40° C.)
  2. washThe organic phase is washed with 25 cm3 of distilled water
  3. dry with materialAfter drying over magnesium sulphate, filtration and concentration under reduced pressure (2 kPa; 40° C.)
  4. customthe residue obtained
  5. customis purified by chromatography under an argon pressure of 50 kPa
  6. washon a column of silica gel (particle size 40-60 μm; diameter 3 cm), eluting with a dichloromethane/methanol mixture (98/2 by volume)
  7. additionThe fractions containing the expected product
  8. customevaporated under reduced pressure (2 kPa; 40° C.)
  9. dry with materialafter drying (90 Pa; 40° C.), 596 mg of N-(6,7-difluoro-1H-indazol-3-yl)butanamide

出典と根拠

ORDレコード
ord-607078b611284eb996ca7a649e48261c
出典データセット
uspto-grants-2005_09
特許番号
US06949579B2

反応ノート

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