Tetrabutylammonium Fluoride → HCID 59514586, compound

HRID 1672151Notes

Reaction equation

[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=3)[N:10]=2)[CH:5]([CH2:22][CH2:23][CH2:24]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:4]1)=[O:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-:53]>C1COCC1>[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=3)[N:10]=2)[CH:5]([CH2:22][CH2:23][CH2:24][F:53])[CH2:4]1)=[O:2]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 3-(4-formyl-1-(6-nitroquinolin-2-yl)piperazin-2-yl)propyl4-methylbenzene-sulfonate 30 (0.056 g, 0.11 mmol) in dry THF (0.30 mL) was treated with a solution of TBAF (0.16 mL, 1 M in THF, 0.16 mmol) to give a dark orange solution. The reaction mixture was heated at 55° C. for 2 h, and then was concentrated in vacuo and diluted with CHCl3. The crude material was purified by column chromatography to give N-Formyl-3-(3-fluoropropyl)-4-(6-nitroquinolin-2-yl)piperazine, 31 as a yellow foam (0.025 g, 64%). 1H NMR (CDCl3, 400 MHz) δ1.60-2.00 (m, 4H), 2.90 (dt, J=3.6 and 12.3 Hz, 0.5H), 3.00 (dd, J=4.2 and 13.3 Hz, 0.5H), 3.20-3.40 (2 m, 2H), 3.44-3.62 (m, 1.5H), 3.72 (bd, 0.5H), 4.32-4.60 (m, 3H), 4.83 (bs, 0.5H), 5.07 (bs, 0.5H), 7.07 (dd, J=3.2 and 9.4 Hz, 1H), 7.69 (m, 1H), 8.03 (d, J=9.1 Hz, 1H), 8.10 (s, 0.5H), 8.25 (s, 0.5H), 8.32 (dd, J=2.6 and 9.1 Hz, 1H), 8.56 (d, J=2.3 Hz, 1H).

Workup

customto give a dark orange solution
concentrationwas concentrated in vacuo
additiondiluted with CHCl3
customThe crude material was purified by column chromatography

Sources & evidence

ORD record: ord-3794ff1bb31b4cbea3f37bfff08a3b8c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998962B2

Reaction notes

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