2-Furancarbonyl chloride → 1-(4-Fluorob-enzyl)-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-6-methyl-2-oxo-1,2-dihydro-quinolin-3-carbonitrile

HRID 346601Notes

Reaction equation

HRID 346601 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[F:9][C:10]1[CH:36]=[CH:35][C:13]([CH2:14][N:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[C:18]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[C:17]([C:32]#[N:33])[C:16]2=[O:34])=[CH:12][CH:11]=1>N1C=CC=CC=1>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[C:18]([N:26]3[CH2:31][CH2:30][N:29]([C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[O:7])[CH2:28][CH2:27]3)=[C:17]([C:32]#[N:33])[C:16]2=[O:34])=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 210818991-(4-Fluoro-benzyl)-6-methyl-2-oxo-4-(piperazin-1-yl)-1,2-dihydro-quinolin-3-carbonitrile

Product 1

HCID 587992381-(4-Fluorob-enzyl)-4-[4-(furan-2-carbonyl)-piperazin-1-yl]-6-methyl-2-oxo-1,2-dihydro-quinolin-3-carbonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Furoyl chloride (118 μL, 1.2 mmol) was added to a stirred solution of Compound 27 (300 mg, 0.8 mmol) in pyridine (5 mL) under argon at 0° C. The solution was allowed to come to room temperature and further stirred overnight. The solution was poured into ice water and the solids formed were filtered. The solids were washed by excess water, dried, and recrystallized by hexane and ether to yield 320 mg (85%) of white solids. M.P. 276° C. 1H NMR (DMSO-d6): δ 2.37 (s, 3H), 3.69 (m, 4H), 3.97 (m, 4H), 5.45 (s, 2H), 6.67 (dd, J=1.7, 3.7 Hz, 1H), 7.09 (d, J=3.4 Hz, 1H), 7.12 (m, 2H), 7.26 (m, 2H), 7.35 (d, J=8.7 Hz, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.71 (s, 1H), 7.89 (s, 1H). EIMS m/z 493 (M+23). Anal. (C27H23FN4O3) C, H, N.

Workup

  1. customto come to room temperature
  2. customthe solids formed
  3. filtrationwere filtered
  4. washThe solids were washed by excess water
  5. customdried
  6. customrecrystallized by hexane and ether

Sources & evidence

ORD record
ord-76f26e307efc4754a2d96647dc10ded1
Source dataset
uspto-grants-2007_02
Patent number
US07173036B2

Reaction notes

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