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-3-yloxy)ethyl]amino]ethyl]-8-iodo-[1,6]naphthyridine-2-carboxamide

HRID 2273649Notes

Reaction equation

HRID 2273649 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:15][CH3:16])[CH2:5][CH2:6][O:7][C:8]1[C:9]([F:14])=[N:10][CH:11]=[CH:12][CH:13]=1.[I:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]2[C:27]=1[N:26]=[C:25]([C:28](OCC)=[O:29])[CH:24]=[CH:23]2.C(N(CCNC(C1C=NC2C(=CC=C(I)C=2)N=1)=O)CCOC1C(F)=NC=CC=1)C>>[CH2:15]([N:4]([CH2:3][CH2:2][NH:1][C:28]([C:25]1[CH:24]=[CH:23][C:22]2[C:27](=[C:18]([I:17])[CH:19]=[N:20][CH:21]=2)[N:26]=1)=[O:29])[CH2:5][CH2:6][O:7][C:8]1[C:9]([F:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:16]

Participants

4

Reactant 3

HCID 44194028N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamideHCID 45258965N-(2-aminoethyl)-N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amineHCID 53485590Ethyl 8-iodo-1,6-naphthyridine-2-carboxylate

Product 1

HCID 52952164N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-8-iodo-[1,6]naphthyridine-2-carboxamideYield 96.8%

Procedure

This compound was prepared, starting from compound 5 (100 mg, 0.44 mmol) and ethyl 8-iodo-[1,6]naphthyridine-2-carboxylate (72) (102 mg, 0.31 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 73 (151 mg, 0.30 mmol) as a yellow oil. Yield 96%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.65; IR (CCl4) ν 1467, 1518, 1685, 2700-3000 cm−: 1H NMR (200 MHz, CDCl3) δ 1.10 (t, 3H, J=7.1 Hz), 2.71 (q, 2H, J=7.1 Hz), 2.83 (t, 2H, J=6.0 Hz), 2.97 (t, 2H, J=5.6 Hz), 3.59 (q, 2H, J=6.0 Hz), 4.12 (t, 2H, J=5.6 Hz), 6.82 (ddd, 1H, 5JH-F=0.5 Hz, J=4.8, 7.9 Hz), 7.12 (ddd, 1H, 4JH-F=10.1 Hz, J=1.6, 7.9 Hz), 7.43 (td, 1H, 4JH-F=1.6 Hz, J=1.6, 4.8 Hz), 8.32 (d, 1H, J=8.4 Hz), 8.40 (d, 1H, J=8.4 Hz), 8.79 (m, 1H), 9.10 (s, 1H), 9.13 (s, 1H); ESI-MS m/z 509.9 [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-3c7ea06550224defb6731973216a334e
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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