2-Methanesulfonylbenzene-1-sulfonyl chloride → HCID 22567132、化合物

HRID 25453ノート

反応式

HRID 25453 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](Cl)(=[O:13])=[O:12])(=[O:4])=[O:3].[NH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][C:24]=1[CH3:25])[NH:21][N:20]=[C:19]2[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>N1C=CC=CC=1.O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][C:24]=1[CH3:25])[NH:21][N:20]=[C:19]2[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:13])=[O:12])(=[O:4])=[O:3]

参加物

5

反応物 2

HCID 27351782-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 225673305-amino-6-methyl-3-phenyl-1H-indazole

生成物 1

HCID 22567132HCID 22567132、化合物収率 34.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

2-Methylsulfonyl-N-(6-methyl-3-phenyl-1H-indazol-5-yl)benzenesulfonamide can be obtained in the following way: 0.45 g of 2-methylsulfonylbenzenesulfonyl chloride is added to a solution, at a temperature in the region of 0° C. and under argon, of 0.4 g of 5-amino-6-methyl-3-phenyl-1H-indazole in 35 ml of pyridine. The reaction mixture is then stirred for 10 minutes at a temperature in the region of 0° C. then 16 hours at a temperature in the region of 20° C., and is then diluted with 50 ml of water. After settling out, the aqueous phase is extracted with 50 ml and then 25 ml of ethyl acetate. The organic extracts are pooled, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue thus obtained is purified by chromatography on a silica column (particle size 63-200 μm), eluting with a dichloromethane/methanol (99/1 by volume) mixture. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up and recrystallized from 20 ml of diethyl ether. The crystals are filtered off through sintered glass, washed with 2 times 10 ml of diisopropyl ether, partially dried and then dried under reduced pressure (3 kPa) at a temperature in the region of 50° C. 0.27 g of 2-methylsulfonyl-N-(6-methyl-3-phenyl-1H-indazol-5-yl)benzenesulfonamide are obtained in the form of a beige powder melting at 239° C. (analysis C21H19N3O4S2 % calculated C, 57.13; H, 4.34; N, 9.52; O, 14.49; S, 14.52. % found C, 56.66; H, 4.52; N, 9.41; S, 14.15).

後処理

  1. extractionthe aqueous phase is extracted with 50 ml
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  5. customThe residue thus obtained
  6. customis purified by chromatography on a silica column (particle size 63-200 μm)
  7. washeluting with a dichloromethane/methanol (99/1 by volume) mixture
  8. additionThe fractions containing the expected product
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  10. customrecrystallized from 20 ml of diethyl ether
  11. filtrationThe crystals are filtered off through sintered glass
  12. washwashed with 2 times 10 ml of diisopropyl ether
  13. custompartially dried
  14. customdried under reduced pressure (3 kPa) at a temperature in the region of 50° C

出典と根拠

ORDレコード
ord-003a62c4793649c98f0c4a4961a71aac
出典データセット
uspto-grants-2005_02
特許番号
US06858638B2

反応ノート

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