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 1745793노트

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HRID 1745793 반응식
[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

참가 물질

5

반응물 3

HCID 7302Gamma-ButyrolactoneHCID 24758Sodium hydrideHCID 178513288HCID 178513288, 화합물

생성물 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-one수율 65.7%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
23 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4e87d21630904cc59b9f649a4cf93024
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07018998B2

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