1-(Thien-2-ylcarbonyl)piperazine → 1-(4-Fluorobenzyl)-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

HRID 970472Notes

Reaction equation

HRID 970472 reaction equation
[N:1]1([C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:17](=[O:33])[C:16]=1[C:34]#[N:35]>C1(C)C=CC=CC=1>[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([N:4]3[CH2:5][CH2:6][N:1]([C:7]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[O:8])[CH2:2][CH2:3]3)=[C:16]([C:34]#[N:35])[C:17]2=[O:33])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 210819574-Chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

Product 1

HCID 210818871-(4-Fluorobenzyl)-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Piperazine-1-yl-thiophen-2-yl-methanone (234 mg, 1.19 mmol) was added to a solution of Compound 8 (170 mg, 0.54 mmol) in toluene (40 mL) and heated overnight at 120° C. The solvent was removed under vacuum. The residue was suspended in water, sonicated, and filtered to yield 247 mg (97%) of white solids. M.P. 258° C. 1H NMR (DMSO-d6): δ 3.69 (m, 4H), 3.94 (m, 4H), 5.47 (s, 2H), 7.16 (m, 3H), 7.28 (m, 3H), 7.43 (d, J=8.5 Hz, 1H), 7.50 (d, J=3.3 Hz, 1H), 7.64 (t, J=7.25, 2H), 7.81 (d, J=4.8 Hz, 1H) 7.95 (d, J=7.5 Hz, 1H). EIMS m/z 473 (M+1), 495 (M+23). Anal. (C26H21FN4O2S) C, H, N.

Workup

  1. customThe solvent was removed under vacuum
  2. customsonicated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2b65e26d6be749b396d7e8b6859ae13e
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

Loading…