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]-6-iodonaphthalene-2-carboxamide

HRID 2273647Notes

Reaction equation

HRID 2273647 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]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:28](OCC)=[O:29])[CH:22]=[CH:21]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:23]1[CH:22]=[CH:21][C:20]2[C:25](=[CH:26][CH:27]=[C:18]([I:17])[CH:19]=2)[CH:24]=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 58151998Ethyl 6-iodonaphthalene-2-carboxylate

Product 1

HCID 52952163N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodonaphthalene-2-carboxamideYield 60%

Procedure

This compound was prepared, starting from compound 5 (200 mg, 0.88 mmol) and ethyl 6-iodonaphthalene-2-carboxylate (69) (194 mg, 0.62 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 12 h; the purification was performed using column chromatography (Al2O3, CH2C2/EtOH, 99.5/0.5, v/v) to give compound 70 (188 mg, 0.37 mmol) as a brown oil. Yield 60%; Rf (Al2O3, CH2Cl2/EtOH, 99.5/0.5, v/v) 0.47; IR (CCl4) ν 1121, 1188, 1246, 1283, 1465, 1515, 1662, 2700-3000, 3250-3400 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.10 (t, 3H, J=7.1 Hz), 2.73 (q, 2H, J=7.1 Hz), 2.84 (t, 2H, J=5.7 Hz), 2.99 (t, 2H, J=5.2 Hz), 3.60 (q, 2H, J=5.7 Hz), 4.11 (t, 2H, J=5.2 Hz), 7.00 (ddd, 1H, 5JH-F=0.7 Hz, J=4.9, 7.9 Hz), 7.14 (m, 1H), 7.19 (ddd, 1H, 4JH-F=10.0 Hz, J=1.7, 7.9 Hz), 7.55 (d, 1H, J=8.6 Hz), 7.65 (m, 1H), 7.66 (d, 1H, J=8.9 Hz), 7.73 (dd, 1H, J=1.9, 8.9 Hz), 7.94 (dd, 1H, J=1.9, 8.9 Hz), 8.23 (se, 2H); ESI-MS m/z 507.9 [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-8455fa1851c348488490245826cb31e9
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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