N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → N-[2-[N-[2-[(6-bromopyridin-2-yl)amino]ethyl]-N-(ethyl)amino]ethyl]-6-iodoquinoxaline-2-carboxamide

HRID 2273643Notes

Reaction equation

HRID 2273643 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=1)[CH2:5][CH3:6].C(N(CCN[C:33]([C:35]1[CH:44]=[N:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([I:45])[CH:41]=2)[N:36]=1)=[O:34])CCOC1C(F)=NC=CC=1)C>>[Br:16][C:12]1[N:11]=[C:10]([NH:9][CH2:8][CH2:7][N:4]([CH2:3][CH2:2][NH:1][C:33]([C:35]2[CH:44]=[N:43][C:42]3[C:37](=[CH:38][CH:39]=[C:40]([I:45])[CH:41]=3)[N:36]=2)=[O:34])[CH2:5][CH3:6])[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 44194028N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamideHCID 86651176N-(2-aminoethyl)-N-[2-[N-(6-bromopyridin-2-yl)amino]ethyl]-N-ethylamine

Product 1

HCID 58152043N-[2-[N-[2-[(6-bromopyridin-2-yl)amino]ethyl]-N-(ethyl)amino]ethyl]-6-iodoquinoxaline-2-carboxamideYield 70%

Procedure

This compound was prepared, starting from compound 62 (120 mg, 0.42 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 7 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 63 (166 mg, 0.33 mmol) as a yellow solid. Yield 70%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.34; mp 49-51° C.; IR (KBr) ν 1160, 1594, 1671, 2750-3000, 3200-3400 cm−1: 1H NMR (400 MHz, CDCl3) δ 1.04 (t, 3H, J=7.1 Hz), 2.64 (q, 2H, J=7.1 Hz), 2.74 (m, 4H), 3.27 (q, 2H, J=5.3 Hz), 3.57 (q, 2H, J=5.8 Hz), 5.32 (m, 1H), 6.16 (d, 1H, J=8.1 Hz), 6.56 (d, 1H, J=7.4 Hz), 7.05 (t, 1H, J=7.8 Hz), 7.81 (d, 1H, J=8.8 Hz), 8.05 (dd, 1H, J=1.9, 8.8 Hz), 8.25 (m, 1H), 8.55 (d, 1H, J=1.9 Hz), 9.58 (s, 1H); ESI-MS m/z 568.9 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time
  3. temperatureunder reflux
  4. custom7 h
  5. customthe purification

Sources & evidence

ORD record
ord-3e26a7268cd148a8bbd9fbee8657ebcd
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

Loading…