4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-2-carboxamide → N-[2-(diethylamino)ethyl]-4-fluoro-6-iodoquinoline-2-carboxamide

HRID 2273669Notes

Reaction equation

HRID 2273669 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[C:4]([C:13]([NH:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:14])[CH:3]=1.C(N(CC)CCNC(C1C=C(I)C=C2C=1N=CC=C2[F:41])=O)C>>[CH2:19]([N:18]([CH2:21][CH3:22])[CH2:17][CH2:16][NH:15][C:13]([C:4]1[CH:3]=[C:2]([F:41])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=1)=[O:14])[CH3:20]

Participants

3

Reactant 2

HCID 581519944-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-2-carboxamideHCID 66945069N-[2-(diethylamino)ethyl]-4-fluoro-6-iodoquinoline-8-carboxamide

Product 1

HCID 58152015N-[2-(diethylamino)ethyl]-4-fluoro-6-iodoquinoline-2-carboxamideYield 48%

Procedure

This compound was prepared, starting from compound 105 (1.00 g, 2.32 mmol), according to the procedure developed for compound 102. Reaction time at 200° C.: 2 h, reaction time at 140° C.: 5 h; the purification was performed using column chromagraphie (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 106 (458 mg, 1.10 mmol) as a yellow solid. Yield 48%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.42; mp 58-60° C.; IR (KBr) ν 1342, 1486, 1518, 1555, 1681, 2760, 2966, 3385 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.06 (t, 6H, J=7.1 Hz), 2.56 (q, 4H, J=7.1 Hz), 2.69 (t, 2H, J=6.1 Hz), 3.54 (q, 2H, J=6.1 Hz), 7.76 (dd, 1H, 5JH-F=1.2 Hz, J=8.9 Hz), 7.96 (m, 2H), 8.42 (d, 1H, J=1.7 Hz), 8.50 (m, 1H); ESI-MS m/z 415.9 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time at 200° C.
  3. custom2 h, reaction time at 140° C.
  4. custom5 h
  5. customthe purification

Sources & evidence

ORD record
ord-f9d08ae7f234437b94728cfff44b2983
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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