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 902495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902495
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 167425624-(3-Fluoro-benzyl)-5-oxo-7-piperazin-1-yl-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl esterAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9bdef09a7e1b408e8ef65aff957f3c1b
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365200B2

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