Water → 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606954

反応式

HRID 1606954 の反応式
[Cl:1][C:2]1[C:7]2[CH2:8][N:9]([CH3:20])[CH2:10][C:11]3[N:12]([C:13](=O)[NH:14][C:15]=3/[CH:16]=[CH:17]\Cl)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[OH2:32]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:32])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[CH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867433567-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine--one

生成物 1

HCID 198515337-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

20.2 g (65.5 mmol) of 7-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine--one was heated to boiling under reflux for 5 hours together with 11.7 ml (78.5 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 200 ml of N,N-dimethylformamide. The reaction mixture was subsequently poured into 800 ml of water and extracted four time with methylene chloride. The organic extracts were washed four times with water, dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel while eluting with ethyl acetate and two successive crystallizations from acetonitrile and from ethyl acetate there was obtained 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 201°-202°.

後処理

  1. extractionextracted four time with methylene chloride
  2. washThe organic extracts were washed four times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. washAfter chromatography of the residue on silica gel while eluting with ethyl acetate and two successive crystallizations from acetonitrile and from ethyl acetate

出典と根拠

ORDレコード
ord-cbbe1afd9e4849a7a994b5b2448f4990
出典データセット
uspto-grants-1989_09
特許番号
US04863920

関連ノート

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