1-(Thien-2-ylcarbonyl)piperazine → 1-Benzyl-6-methyl-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

HRID 970487Notes

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.C1([NH:20][C:21]([C:23]2[C:24](=[O:36])[N:25]([CH3:35])[C:26]3[C:31]([C:32]=2O)=[CH:30][C:29]([CH3:34])=[CH:28][CH:27]=3)=O)CCCCC1>C1(C)C=CC=CC=1>[CH2:35]([N:25]1[C:26]2[C:31](=[CH:30][C:29]([CH3:34])=[CH:28][CH:27]=2)[C:32]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)=[O:8])[CH2:2][CH2:3]2)=[C:23]([C:21]#[N:20])[C:24]1=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 110 °C

Procedure

piperazine-1-yl-thiophen-2-yl-methanone (490 mg, 2.5 mmol) was added to a solution of Compound 20 (309 mg, 1 mmol) in toluene (20 mL) and heated overnight at 110° C. The solvent was removed under vacuum. The residue was suspended in water, sonicated, and filtered. The crude product was purified by flash chromatography eluting with 0-2% methanol in dichloromethane gradient to yield 362 mg (77%) of white solids. M.P. 183° C. 1H NMR (DMSO-d6): δ 2.36 (s, 3H), 3.69 (m, 4H), 3.94 (m, 4H), 5.47 (s, 2H), 7.16-7.20 (m, 4H), 7.23-7.33 (m, 3H), 7.44 (d, J=8.8 Hz, 1H), 7.50 (d, J=3.8 Hz, 1H), 7.70 (s, 1H), 7.81 (d, J=4.8 Hz, 1H). EIMS m/z 491 (M+23). Anal. (C27H24N4O2S) C,H, N.

Workup

customThe solvent was removed under vacuum
customsonicated
filtrationfiltered
customThe crude product was purified by flash chromatography
washeluting with 0-2% methanol in dichloromethane gradient

Sources & evidence

ORD record: ord-d8924c1ae48c4fb99742ae0ce1264b18
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312220B2

Reaction notes

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