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Dichloromethane → 6-(7-Chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-oxo-5H-pyrrole(3,4-b)pyrazin-5-yl dimethylcarbamate

HRID 66339
ノート
印刷プレビュー

反応式

HRID 66339 の反応式
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].C(N(CC)CC)C.[Cl:14][C:15]1[N:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([N:25]3[CH:33]([OH:34])[C:32]4[C:27](=[N:28][CH:29]=[CH:30][N:31]=4)[C:26]3=[O:35])=[N:22]2)=[CH:17][CH:16]=1.C(Cl)Cl>C(#N)C.CN(C)C=O.O.N1C=CC=CC=1>[Cl:14][C:15]1[N:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([N:25]3[CH:33]([O:34][C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[C:32]4[C:27](=[N:28][CH:29]=[CH:30][N:31]=4)[C:26]3=[O:35])=[N:22]2)=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 64531286-(7-chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one

生成物 1

HCID 227547576-(7-Chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-oxo-5H-pyrrole(3,4-b)pyrazin-5-yl dimethylcarbamate収率 62.4%

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回
HCID 1049Pyridine溶媒
HCID 6228Dimethylformamide溶媒
HCID 6342Acetonitrile溶媒

実験手順

Dimethylcarbamoyl chloride (4.85 g.) and triethylamine (4.55 g.) are added successively to a suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-5-hydroxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (4.7 g.) in a mixture of anhydrous methylene chloride (47 cc.) and anhydrous pyridine (16 cc.). The reaction mixture is heated at the reflux temperature for 2 hours, and is then cooled and poured into water (180 cc.). A slight amount of insoluble matter is filtered off and the aqueous layer is decanted off and washed with methylene chloride (2 × 50 cc.) by successive decantations. The combined organic layers are washed by successive decantations with 1N sodium hydroxide solution (2 × 30 cc.) and water (2 × 33 cc.), dried with anhydrous sodium sulphate in the presence of decolourising charcoal, filtered and evaporated to dryness under reduced pressure. The residue obtained is taken up in acetonitrile (20 cc.) and the insoluble product is filtered off and washed with acetonitrile (3 × 2 cc.). Recrystallisation of this product from dimethylformamide (14 cc.) gives a solvated product (4.1 g.). This product is dissolved in dimethylformamide (100 cc.) at a temperature of about 70° C. The solution thus obtained is poured into water (1,200 cc.) and the insoluble product is filtered off and washed with water (5 × 20 cc.). After drying, 6-(7-chloro-1,8-naphthyridin-2-yl)-5-dimethylaminocarbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (3.6 g.), melting at 270° C., is obtained.

後処理

  1. temperatureThe reaction mixture is heated at the reflux temperature for 2 hours
  2. temperatureis then cooled
  3. filtrationA slight amount of insoluble matter is filtered off
  4. customthe aqueous layer is decanted off
  5. washwashed with methylene chloride (2 × 50 cc.) by successive decantations
  6. washThe combined organic layers are washed by successive decantations with 1N sodium hydroxide solution (2 × 30 cc.) and water (2 × 33 cc.)
  7. dry with materialdried with anhydrous sodium sulphate in the presence of decolourising charcoal
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure
  10. customThe residue obtained
  11. filtrationthe insoluble product is filtered off
  12. washwashed with acetonitrile (3 × 2 cc.)
  13. customRecrystallisation of this product from dimethylformamide (14 cc.)
  14. customgives a solvated product (4.1 g.)
  15. customThe solution thus obtained
  16. filtrationthe insoluble product is filtered off
  17. washwashed with water (5 × 20 cc.)
  18. customAfter drying

出典と根拠

ORDレコード
ord-9a3b6c1266164486843ea24d1d38d68f
出典データセット
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04131674

反応ノート

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