Heptafluorobutyryl Chloride → N-[6-chloro-1H-indazol-3-yl]-2,2,3,3,4,4,4-heptafluorobutanamide

HRID 497669

反応式

HRID 497669 の反応式
[F:1][C:2]([F:13])([C:9]([F:12])([F:11])[F:10])[C:3]([F:8])([F:7])[C:4](Cl)=[O:5].[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([NH2:24])=[N:20][NH:21]2)=[CH:17][CH:16]=1>N1C=CC=CC=1>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([NH:24][C:4](=[O:5])[C:3]([F:8])([F:7])[C:2]([F:13])([F:1])[C:9]([F:12])([F:11])[F:10])=[N:20][NH:21]2)=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 67810Heptafluorobutyryl ChlorideHCID 856286-chloro-1H-indazol-3-amine

生成物 1

HCID 22319502N-[6-chloro-1H-indazol-3-yl]-2,2,3,3,4,4,4-heptafluorobutanamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
6 °C

実験手順

0.60 cm3 of heptafluorobutyryl chloride is added to 1 g of 6-chloro-1H-indazole-3-amine in 10 cm3 of pyridine, after cooling the medium to about 6° C., the mixture is then allowed to return to room temperature over 19 hours and is evaporated to dryness under reduced pressure (2 kPa; 45° C.). The residue is taken up in 40 cm3 of ethyl acetate and 20 cm3 of water; the precipitate formed is filtered off on a sinter funnel and then rinsed with 2×10 cm3 of methylene chloride and purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.) to give 0.77 g of N-[6-chloro-1H-indazol-3-yl]-2,2,3,3,4,4,4-heptafluorobutanamide in cottony form.

後処理

  1. customis evaporated to dryness under reduced pressure (2 kPa; 45° C.)
  2. customthe precipitate formed
  3. filtrationis filtered off on a sinter funnel
  4. washrinsed with 2×10 cm3 of methylene chloride
  5. custompurified by chromatography under an argon pressure of 50 kPa
  6. washon a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  7. additionThe fractions containing the expected product
  8. customevaporated under reduced pressure (2 kPa; 50° C.)

出典と根拠

ORDレコード
ord-de4280bf980547e79b0f3ae124c4f49f
出典データセット
uspto-grants-2005_09
特許番号
US06949579B2

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