1-(6-Fluoro-2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)ethanone → 1-(6-Fluoro-3-(isopropylamino)-2-methylquinoxalin-5-yl)ethanone

HRID 1056119Notes

Reaction equation

HRID 1056119 reaction equation
[F:1][C:2]1[C:3]([C:18](=[O:20])[CH3:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([NH:13][C:14]1(C)[CH2:16][CH2:15]1)=[N:5]2.BrC1C(F)=CC=C2C=1N=C(NC(C)C)C(C)=N2>>[F:1][C:2]1[C:3]([C:18](=[O:20])[CH3:19])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([NH:13][CH:14]([CH3:16])[CH3:15])=[N:5]2

Participants

3

Reactant 2

HCID 897818741-(6-Fluoro-2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)ethanoneHCID 897821228-bromo-7-fluoro-N-isopropyl-3-methylquinoxalin-2-amine

Product 1

HCID 897820211-(6-Fluoro-3-(isopropylamino)-2-methylquinoxalin-5-yl)ethanoneYield 90%

Procedure

1-(6-Fluoro-3-(isopropylamino)-2-methylquinoxalin-5-yl)ethanone (619b) (3.58 g, 90% yield) as an orange solid was prepared according to the procedures described for Intermediate 610b, using 8-bromo-7-fluoro-N-isopropyl-3-methylquinoxalin-2-amine (373a) (2.00 g, 6.70 mmol) as the starting material. 19F NMR (377 MHz, DMSO-d6) δ ppm −116.42. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80 (1H, dd, J=9.0, 6.1 Hz), 7.20 (1H, t, J=9.2 Hz), 7.01 (1H, d, J=7.4 Hz), 4.23 (1H, m), 2.66 (3H, s), 2.52 (3H, s), 1.26 (6H, d, J=6.7 Hz). m/z (ESI, +ve) 262.1 (M+H)+.

Sources & evidence

ORD record
ord-25db5af77b2a452fbf8fd30d93f73dcf
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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