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 902495Notes

Reaction equation

HRID 902495 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9bdef09a7e1b408e8ef65aff957f3c1b
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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