Sodium hydride → 5-(4-Acetylpiperazin-1-yl)carbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrrole

HRID 27085ノート

反応式

HRID 27085 の反応式
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:16]([OH:17])[C:15]4[S:18][CH2:19][CH2:20][S:21][C:14]=4[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:25]([N:28]1[CH2:33][CH2:32][N:31]([C:34](Cl)=[O:35])[CH2:30][CH2:29]1)(=[O:27])[CH3:26]>CN(C)C=O.O.C(Cl)(Cl)Cl>[C:25]([N:28]1[CH2:33][CH2:32][N:31]([C:34]([O:17][CH:16]2[N:12]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[N:11][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]=3)[C:13](=[O:22])[C:14]3[S:21][CH2:20][CH2:19][S:18][C:15]2=3)=[O:35])[CH2:30][CH2:29]1)(=[O:27])[CH3:26]

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 30347196-(7-Chloro-1,8-naphthyridin-2-yl)-2,3,6,7-tetrahydro-7-hydroxy-5H-1,4-dithiino[2,3-c]pyrrol-5-oneHCID 13728618HCID 13728618、化合物

生成物 1

HCID 137286255-(4-Acetylpiperazin-1-yl)carbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrrole収率 38.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
2 °C

実験手順

6-(7-Chloro-1,8-naphthyridin-2-yl)-5-hydroxy-7-oxo-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrrole (2.5 g.) is added, at 0° C., to a suspension of sodium hydride (0.20 g.) in anhydrous dimethylformamide (10 cc.). The reaction mixture is stirred for 1 hour at 2° C., and then a solution of 1-acetyl-4-chlorocarbonylpiperazine (2.85 g.) in anhydrous dimethylformamide (20 cc.) is added. After 18 hours at 2° C., the reaction mixture is diluted with distilled water (100 cc.). The precipitate formed is filtered off, washed with distilled water (10 cc.) and dried in air. The product obtained (3.5 g.) is dissolved in chloroform (50 cc.), and the solution is filtered through silica gel (50.0 g.) contained in a column of diameter 4.1 cm. Elution is carried out using a mixture of chloroform and methanol (98-2 by volume; 400 cc.), and the eluate is discarded. Elution is continued using a similar mixture (400 cc). This eluate is evaporated to dryness under reduced pressure (20 mm.Hg). The chromatographed product is purified by recrystallisation from a mixture of dimethylformamide and ethanol (50-50 by volume; 20 cc.). 5-(4-Acetylpiperazin-1-yl)carbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-dithiino[2,3-c]pyrrole (1.40 g.), which melts at 271° C., is obtained.

後処理

  1. waitAfter 18 hours at 2° C.
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with distilled water (10 cc.)
  5. customdried in air
  6. customThe product obtained (3.5 g.)
  7. filtrationthe solution is filtered through silica gel (50.0 g.)
  8. washElution
  9. additiona mixture of chloroform and methanol (98-2 by volume; 400 cc.)
  10. washElution
  11. customThis eluate is evaporated to dryness under reduced pressure (20 mm.Hg)
  12. customThe chromatographed product is purified by recrystallisation from a mixture of dimethylformamide and ethanol (50-50 by volume; 20 cc.)

出典と根拠

ORDレコード
ord-2f7b6daa79bd4d5683bd4907a9d0c2ba
出典データセット
uspto-grants-1980_09
特許番号
US04220646

反応ノート

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