Butyl isocyanate → 5-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

HRID 66346ノート

反応式

HRID 66346 の反応式
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[Cl:8][C:9]1[N:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([N:19]3[CH:27]([OH:28])[C:26]4[C:21](=[N:22][CH:23]=[CH:24][N:25]=4)[C:20]3=[O:29])=[N:16]2)=[CH:11][CH:10]=1>C(#N)C.C(Cl)Cl>[CH2:1]([NH:5][C:6]([O:28][CH:27]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[C:20](=[O:29])[N:19]1[C:15]1[CH:14]=[CH:13][C:12]2[C:17](=[N:18][C:9]([Cl:8])=[CH:10][CH:11]=2)[N:16]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 2

HCID 8110Butyl isocyanateHCID 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 227547395-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine収率 50.7%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

n-Butyl isocyanate (5 g.) is added 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 (7.8 g.) in anhydrous acetonitrile (156 cc.) and the mixture is heated at the reflux temperature for 7 hours. The insoluble product is filtered off and washed with anhydrous acetonitrile (2 × 10 cc.). The product obtained is dissolved in methylene chloride (430 cc.) and the resulting solution is washed by successive decantations with 0.1N sodium hydroxide solution (85 cc.) and water (85 cc.). After drying, the organic phase is concentrated to dryness under reduced pressure (20 mm.Hg). Recrystallisation of the residue obtained, from acetonitrile (230 cc.), gives 5-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (5.2 g.) melting at 264° C.

後処理

  1. temperaturethe mixture is heated at the reflux temperature for 7 hours
  2. filtrationThe insoluble product is filtered off
  3. washwashed with anhydrous acetonitrile (2 × 10 cc.)
  4. customThe product obtained
  5. washthe resulting solution is washed by successive decantations with 0.1N sodium hydroxide solution (85 cc.) and water (85 cc.)
  6. customAfter drying
  7. concentrationthe organic phase is concentrated to dryness under reduced pressure (20 mm.Hg)
  8. customRecrystallisation of the residue
  9. customobtained, from acetonitrile (230 cc.)

出典と根拠

ORDレコード
ord-65ef33cd3a3346ebafe6a0f52c079033
出典データセット
uspto-grants-1978_12
特許番号
US04131674

反応ノート

読み込み中…