N-[2-[N-ethyl-N-[2-[[(2-fluoropyridin-4-yl)carbonyl]amino]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 dihydrochloride salt

HRID 2273633Notes

Reaction equation

HRID 2273633 reaction equation
[CH2:1]([N:3]([CH2:16][CH2:17][NH:18][C:19]([C:21]1[CH:30]=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:31])[CH:27]=2)[N:22]=1)=[O:20])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([F:15])[CH:10]=1)=[O:8])[CH3:2].[ClH:32].Cl.C(N(CCNC(C1C=NC2C(=CC=C(I)C=2)N=1)=O)CCOC1C(F)=NC=CC=1)C>>[ClH:32].[ClH:32].[CH2:1]([N:3]([CH2:16][CH2:17][NH:18][C:19]([C:21]1[CH:30]=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:31])[CH:27]=2)[N:22]=1)=[O:20])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][N:12]=[C:11]([F:15])[CH:10]=1)=[O:8])[CH3:2]

Participants

3

Reactant 2

HCID 44183723N-[2-[N-ethyl-N-[2-[[(2-fluoropyridin-4-yl)carbonyl]amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamideHCID 52952259n-[2-[n-Ethyl-n-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt

Product 1

HCID 52952258N-[2-[N-ethyl-N-[2-[[(2-fluoropyridin-4-yl)carbonyl]amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride saltYield 84%

Procedure

This compound was prepared, starting from compound 39 (158 mg, 0.30 mmol), according to the procedure developed for compound 11. Reaction time at room temperature: 12 h to give compound 40 (152 mg, 0.25 mmol) as a very hygroscopic beige solid. Yield 84%; mp 157-159° C.; IR (KBr) ν 1163, 1228, 1308, 1402, 1475, 1535, 1690, 2400-2700, 2800-3100, 3200-3500 cm−1; 1H NMR (200 MHz, DMSO-d6) δ 1.28 (t, 3H, J=6.7 Hz), 3.37 (m, 6H, J=7.1 Hz), 3.77 (m, 4H), 7.57 (s, 1H), 7.75 (d, 1H, J=5.0 Hz), 7.86 (d, 1H, J=8.8 Hz), 8.21 (dd, 1H, J=1.7, 8.8 Hz), 8.32 (d, 1H, J=5.0 Hz), 8.59 (d, 1H, J=1.7 Hz), 9.39 (s, 1H), 9.42 (m, 2H), 10.58 (se, 1H); ESI-MS m/z 537.0 [M+H]+; Anal. Calcd for C21H22O2IN6F, 2HCl: C, 41.40; H, 3.97; N, 13.79. Found: C, 42.67; H, 4.39; N, 13.66.

Workup

  1. customThis compound was prepared
  2. customReaction time at room temperature

Sources & evidence

ORD record
ord-f21b1e08b3944e22babd3aab4aa63583
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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