2-Butanamine, 2-methyl- → 8-bromo-7-fluoro-3-methyl-N-(tert-pentyl)quinoxalin-2-amine

HRID 1056255Notes

Reaction equation

HRID 1056255 reaction equation
[Br:1][C:2]1[C:3]([F:18])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([CH3:17])=[N:7]2.Br[C:20]1C(F)=CC=C2C=1NC(=O)C(C)=N2.C(N)(CC)(C)C>CS(C)=O>[Br:1][C:2]1[C:3]([F:18])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH2:14][CH3:20])([CH3:15])[CH3:16])[C:8]([CH3:17])=[N:7]2

Participants

5

Reactant 3

HCID 689862-Butanamine, 2-methyl-HCID 897819348-bromo-N-(tert-butyl)-7-fluoro-3-methylquinoxalin-2-amineHCID 897842068-bromo-7-fluoro-3-methylquinoxalin-2(1H)-one

Product 1

HCID 897819178-bromo-7-fluoro-3-methyl-N-(tert-pentyl)quinoxalin-2-amineYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound (580 mg, 1.78 mmol, 81% yield) as an orange amorphous solid was prepared according to the procedure described for Intermediate 605a, using 5-bromo-3-chloro-6-fluoro-2-methylquinoxaline (600) (607 mg, 2.20 mmol) and tert-amylamine (Aldrich Chemical Company) (1.29 mL, 11.02 mmol) in DMSO (5.0 mL) as the starting materials. 1H NMR (400 MHz, CDCl3) δ ppm 7.75 (1H, dd, J=9.0, 5.7 Hz), 7.15 (1H, t, J=8.7 Hz), 4.74 (1H, br. s.), 2.54 (3H, s), 2.09 (2H, q, J=7.4 Hz), 1.58 (6H, s), 0.88 (3H, t, J=7.5 Hz). 19F NMR (376 MHz, CDCl3) δ ppm −103.39 (1F, s). m/z (ESI, +ve ion) 326.0/328.0.

Sources & evidence

ORD record
ord-0eba3c68286d4243944bde1027295e21
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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