Gamma-Butyrolactone → 8-(4-Fluoro-phenyl)-4-{3-[5-(3-hydroxy-propyl)-[1,2,4]oxadiazol-3-yl]-phenyl}-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1062256ノート

反応式

HRID 1062256 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]=[C:13]([C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=4)[C:21]([NH:23][OH:24])=[NH:22])[CH2:14][C:15](=[O:17])[NH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:32]1(=O)[O:36][CH2:35][CH2:34][CH2:33]1>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]=[C:13]([C:18]4[CH:27]=[CH:26][CH:25]=[C:20]([C:21]5[N:22]=[C:32]([CH2:33][CH2:34][CH2:35][OH:36])[O:24][N:23]=5)[CH:19]=4)[CH2:14][C:15](=[O:17])[NH:16][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 7302Gamma-ButyrolactoneHCID 24758Sodium hydrideHCID 178513288HCID 178513288、化合物

生成物 1

HCID 222245998-(4-Fluoro-phenyl)-4-{3-[5-(3-hydroxy-propyl)-[1,2,4]oxadiazol-3-yl]-phenyl}-1,3-dihydro-benzo[b][1,4]diazepin-2-one収率 65.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
23 °C

実験手順

To a stirred suspension of 3-[7-(4-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-N-hydroxy-benzamidine (Example 167) (78 mg, 0.2 mmol) in EtOH (3 mL) was added at 23° C. sodium hydride (55% dispersion in oil, 32 mg, 0.8 mmol) and the mixture was stirred at 23° C. for 5 min. Butyrolactone (103 mg, 1.2 mmol) was added and the mixture was heated to 70° C. for 3 h. The reaction mixture was cooled to 23° C. and partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, evaporated in vacuum, and the residue was crystallized from dichloromethane to give the title compound as light yellow solid (60 mg).

後処理

  1. temperaturethe mixture was heated to 70° C. for 3 h
  2. temperatureThe reaction mixture was cooled to 23° C.
  3. custompartitioned between ethyl acetate and H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated in vacuum
  6. customthe residue was crystallized from dichloromethane

出典と根拠

ORDレコード
ord-0318da91ced94d3d8fcf39e452dcc1c0
出典データセット
uspto-grants-2005_11
特許番号
US06960578B2

反応ノート

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