Dimethylformamide → N11-Ethyl-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one

HRID 1898873ノート

反応式

HRID 1898873 の反応式
[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[H-].[Na+].I[CH2:25][CH3:26]>O>[CH2:25]([N:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[NH:10][C:11](=[O:12])[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:6]1=2)[CH3:26]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 4532415H-Pyrido(2,3-b)(1,5)benzodiazepin-5-one, 6,11-dihydro-

生成物 1

HCID 453243N11-Ethyl-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one収率 21%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of 15 g of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one and 150 ml DMF was heated to 50° C. To the slurry was added 7.5 g (2 equiv) of 50% sodium hydride in mineral oil dispersion, during which time the temperature rose to 65° C. The mixture was cooled to 40° C. and then 6.0 ml of iodoethane was added. The resulting mixture was stirred at room temperature overnight, then poured into 700 ml of water and extracted with 700 ml of ether. The ether phase was dried (MgSO4) and concentrated to dryness. The crude product was purified by column chromatography on basic alumina to yield 3.6 g (21% of theory) of 6,11-dihydro-11-ethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, m.p. 210°-220° C.

後処理

  1. customrose to 65° C
  2. temperatureThe mixture was cooled to 40° C.
  3. extractionextracted with 700 ml of ether
  4. dry with materialThe ether phase was dried (MgSO4)
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by column chromatography on basic alumina

出典と根拠

ORDレコード
ord-3a31c605a8f049f8a7f47472c481bc70
出典データセット
uspto-grants-1996_11
特許番号
US05571809

反応ノート

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