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

HRID 2273659Notes

Reaction equation

HRID 2273659 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([F:11])[C:6]=1[CH2:12][NH2:13])[CH3:2].[I:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[C:22]([C:27](OCC)=[O:28])[CH:21]=[N:20]2.C(N(CCNC(C1C=NC2C(=CC=C(I)C=2)N=1)=O)CCOC1C(F)=NC=CC=1)C>>[CH2:14]([N:3]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([F:11])[C:6]=1[CH2:12][NH:13][C:27]([C:22]1[CH:21]=[N:20][C:19]2[C:24](=[CH:25][CH:26]=[C:17]([I:16])[CH:18]=2)[N:23]=1)=[O:28])[CH2:1][CH3:2])[CH3:15]

Participants

4

Reactant 3

HCID 44194028N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamideHCID 52952057N,N-diethyl-N-[(3-aminomethyl-2-fluoropyridin-4-yl)methyl]amineHCID 53485588Ethyl 6-iodoquinoxaline-2-carboxylate

Product 1

HCID 52952161N-[[4-(N,N-diethylaminomethyl)-2-fluoropyridin-3-yl]methyl]-6-iodoquinoxaline-2-carboxamideYield 57%

Procedure

This compound was prepared, starting from compounds 90 (0.70 g, 3.31 mmol) and 9 (1.09 g, 3.31 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 12 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 91 (926 mg, 1.88 mmol) as a beige solid. Yield 57%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.38; mp 147-149° C.; IR (KBr) ν 1160, 1413, 1477, 1508, 1679, 2967 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.13 (t, 6H, J=7.1 Hz), 2.66 (m, 4H), 3.80 (se, 2H), 4.82 (d, 2H, J=6.0 Hz), 7.19 (m, 1H), 7.71 (d, 1H, J=8.8 Hz), 8.02 (dd, 1H, J=1.8, 8.8 Hz), 8.08 (d, 1H, J=4.8 Hz), 8.55 (d, 1H, J=1.8 Hz), 9.14 (m, 1H), 9.61 (s, 1H); ESI-MS m/z 493.9 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time
  3. temperatureunder reflux
  4. custom12 h
  5. customthe purification

Sources & evidence

ORD record
ord-3e18c78ba23d45b085ca8735c89fa131
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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