N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → N-[2-[N-ethyl-N-[2-[[(2-fluoropyridin-4-yl)carbonyl]amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide

HRID 2273632Notes

Reaction equation

HRID 2273632 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:17][CH3:18])[CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([F:16])[CH:11]=1)=[O:9].C(N(CCN[C:35]([C:37]1[CH:46]=[N:45][C:44]2[C:39](=[CH:40][CH:41]=[C:42]([I:47])[CH:43]=2)[N:38]=1)=[O:36])CCOC1C(F)=NC=CC=1)C>>[CH2:17]([N:4]([CH2:3][CH2:2][NH:1][C:35]([C:37]1[CH:46]=[N:45][C:44]2[C:39](=[CH:40][CH:41]=[C:42]([I:47])[CH:43]=2)[N:38]=1)=[O:36])[CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([F:16])[CH:11]=1)=[O:9])[CH3:18]

Participants

3

Reactant 2

HCID 44194028N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamideHCID 529519502-aminoethyl-N-ethyl-N-[2-[[(2-fluoropyridin-4-yl)carbonyl]amino]ethyl]amine

Product 1

HCID 44183723N-[2-[N-ethyl-N-[2-[[(2-fluoropyridin-4-yl)carbonyl]amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamideYield 63%

Procedure

This compound was prepared, starting from compound 38 (0.26 g, 1.02 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 24 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 98/2, v/v) to give compound 39 (236 mg, 0.45 mmol) as a beige solid. Yield 63%; Rf (Al2O3, CH2Cl2/EtOH, 98/2, v/v) 0.50; mp 146-148° C.; IR (KBr) ν 1524, 1542, 1662, 2800-3000, 3335, 3388 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.02 (t, 3H, J=7.1 Hz), 2.65 (q, 2H, J=7.1 Hz), 2.79 (m, 4H), 3.59 (m, 4H), 7.33 (s, 1H), 7.52 (d, 1H, J=5.1 Hz), 7.64 (d, 2H, J=8.8 Hz), 8.01 (dd, 1H, J=1.7, 8.8 Hz), 8.14 (d, 1H, J=5.1 Hz), 8.22 (m, 1H), 8.55 (d, 1H, J=1.7 Hz), 9.48 (s, 1H); ESI-MS m/z 537.0 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time
  3. temperatureunder reflux
  4. custom24 h
  5. customthe purification

Sources & evidence

ORD record
ord-31746825a9c54f3eb90d5b73cf43e241
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

Loading…