Piperazine → 4-(3-Fluoro-benzyl)-5-oxo-7-piperazin-1-yl-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester

HRID 902495노트

반응식

HRID 902495 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:9]2[CH:21]=[CH:22][S:23][C:8]=2[C:7]=1Cl)=[O:5])[CH3:2].[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:9]2[CH:21]=[CH:22][S:23][C:8]=2[C:7]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 4837PiperazineHCID 693126547-Chloro-4-(3-fluoro-benzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester

생성물 1

HCID 167425624-(3-Fluoro-benzyl)-5-oxo-7-piperazin-1-yl-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester수율 84.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

7-Chloro-4-(3-fluoro-benzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (17) (10 g, 27.39 mmol) was added slowly to a solution of piperazine (9.42 g, 109 mmol) in dichloromethane. The solution was stirred at room temperature for 3 h. The solvent was evaporated under vacuum. The residue was suspended in water, stirred vigorously at room temperature, and filtered. The solids were again dissolved in dichloromethane and washed by water. The organic phase was dried over MgSO4 and concentrated to yield 9.63 g (84%) of 4-(3-fluoro-benzyl)-5-oxo-7-piperazin-1-yl-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester. 1H-NMR (DMSO-d6) δ 1.29 (m, 3H), 2.81 (m, 4H), 3.21 (m, 4H), 4.25 (m, 2H), 5.35 (s, 2H), 7.12 (m, 3H), 7.30 (m, 2H), 7.97 (m, 1H); EIMS m/z 416 (M+1).

후처리

  1. customThe solvent was evaporated under vacuum
  2. stirringstirred vigorously at room temperature
  3. filtrationfiltered
  4. dissolutionThe solids were again dissolved in dichloromethane
  5. washwashed by water
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9bdef09a7e1b408e8ef65aff957f3c1b
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365200B2

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