N,N-Diethylethylenediamine → N-[2-(diethylamino)ethyl]-6-iodo-4-oxo-1,4-dihydroquinoline-8-carboxamide

HRID 2273664Notes

Reaction equation

HRID 2273664 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([O:14]C)=O)[CH:11]=1)[NH:8][CH:7]=[CH:6][C:5]2=[O:16].[CH2:17]([N:19]([CH2:23][CH3:24])[CH2:20][CH2:21][NH2:22])[CH3:18].C(N(CCNC(C1C=NC2C(=CC=C(I)C=2)N=1)=O)CCOC1C(F)=NC=CC=1)C>>[CH2:17]([N:19]([CH2:23][CH3:24])[CH2:20][CH2:21][NH:22][C:12]([C:10]1[CH:11]=[C:2]([I:1])[CH:3]=[C:4]2[C:9]=1[NH:8][CH:7]=[CH:6][C:5]2=[O:16])=[O:14])[CH3:18]

Participants

4

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 44194028N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamideHCID 66946161Methyl 6-iodo-4-oxo-1,4-dihydroquinoline-8-carboxylate

Product 1

HCID 66945735N-[2-(diethylamino)ethyl]-6-iodo-4-oxo-1,4-dihydroquinoline-8-carboxamideYield 86.3%

Procedure

This compound was prepared, starting from compound 99 (2.00 g, 6.08 mmol) and N,N-diethylethylenediamine (1.21 mL, 8.56 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 14 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 96/4, v/v) to give compound 100 (2.17 g, 5.25 mmol) as a beige solid. Yield 86%; Rf (Al2O3, CH2Cl2/EtOH, 96/4, v/v) 0.51; mp 141-143° C.; IR (KBr) ν 1392, 1491, 1560, 1617, 1641, 2800-3000, 3293 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.07 (t, 6H, J=7.1 Hz), 2.62 (q, 4H, J=7.1 Hz), 2.71 (t, 2H, J=6.3 Hz), 3.50 (m, 2H), 6.30 (d, 1H, J=7.5 Hz), 7.64 (m, 2H), 8.07 (d, 1H, J=1.9 Hz), 8.79 (d, 1H, J=1.9 Hz); ESI-MS m/z 413.8 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time
  3. temperatureunder reflux
  4. custom14 h
  5. customthe purification

Sources & evidence

ORD record
ord-e30db02d8aac40228da00c38e0ff4518
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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