2-Furancarbonyl chloride → 4-[4-(Furan-2-carbonyl)-piperazin-1-yl]-1,6-dimethyl-2-oxo-1,2-dihydro-quinolin-3-carbonitrile

HRID 970578Notes

Reaction equation

HRID 970578 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[CH3:9][N:10]1[C:19]2[C:14](=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=2)[C:13]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[C:12]([C:27]#[N:28])[C:11]1=[O:29]>N1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:24]1[CH2:25][CH2:26][N:21]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=3)[N:10]([CH3:9])[C:11](=[O:29])[C:12]=2[C:27]#[N:28])[CH2:22][CH2:23]1)=[O:7]

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 210819011,6-Dimethyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-quinoline-3-carbonitrile

Product 1

HCID 210819534-[4-(Furan-2-carbonyl)-piperazin-1-yl]-1,6-dimethyl-2-oxo-1,2-dihydro-quinolin-3-carbonitrileYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Furoyl chloride (148 μL, 1.5 mmol) was added to a stirred solution of Compound 28 (282 mg, 1.0 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 ethyl acetate to yield 221 mg (59%) of white solids. M.P. 231° C. 1H NMR (DMSO-d6): δ 2.41 (s, 3H), 3.56 (s, 3H), 3.63 (m, 4H), 3.95 (m, 4H), 6.66 (dd, J=1.5, 3.6 Hz, 1H), 7.08 (d, J=3.4 Hz, 1H), 7.48 (d, J=8.7 Hz, 1H), 7.59 (dd, J=1.2, 8.8 Hz, 1H), 7.69 (s, 1H), 7.88 (s, 1H). EIMS m/z 399 (M+23). Anal. (C21H20N4O3) 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 ethyl acetate

Sources & evidence

ORD record
ord-87724f35a8e74291a58f3c76dc49292d
Source dataset
uspto-grants-2007_12
Patent number
US07312221B2

Reaction notes

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