Hydrochloric Acid → n-[2-[n-Ethyl-n-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt

HRID 2273621Notes

Reaction equation

HRID 2273621 reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([I:29])[CH:25]=2)[N:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].[ClH:30]>ClCCl.CCOCC>[ClH:30].[ClH:30].[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([I:29])[CH:25]=2)[N:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44194028N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide

Product 1

HCID 52952259n-[2-[n-Ethyl-n-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride saltYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 10 (0.23 g, 0.45 mmol) in anhydrous dichloromethane (5 mL) was added, under argon, a 2.0 N hydrochloric acid solution in anhydrous ether (10 mL). The mixture was stirred at room temperature for 10 min and the solvent was evapored under vacuum. The residue was then suspended in anhydrous ether (10 mL) and the mixture was stirred, under argon, at room temperature for one night. The precipitate was collected by filtration to give compound 11 (0.24 g, 0.41 mmol) as a very hygroscopic beige solid. Yield 91%; mp 99-101° C. (dec.); IR (KBr) ν 1464, 1533, 1560, 1671, 2400-2700, 2800-3100, 3200-3400 cm−1; 1H NMR (200 MHz, DMSO-d6) δ 1.31 (t, 3H, J=7.0 Hz), 3.40 (m, 4H), 3.78 (m, 4H), 4.19 (m, 6H), 4.55 (t, 2H, J=3.5 Hz), 7.28 (dd, 1H, J=5.3, 7.7 Hz), 7.70 (m, 2H), 7.90 (d, 1H, J=8.8 Hz), 8.25 (dd, 1H, J=1.9, 8.8 Hz), 8.64 (d, 1H, J=1.8 Hz), 9.40 (m, 2H), 10.53 (se, 1H); ESI-MS m/z 509.9 [M+H]+; Anal. Calcd for C20H21O2IN5F, 2HCl, H2O: C, 40.02; H, 4.20; N, 11.67. Found: C, 40.40; H, 4.34; N, 11.28.

Workup

  1. stirringthe mixture was stirred, under argon, at room temperature for one night
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-85818f642b844f8cae463266d780bad8
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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