Diisopropylethylamine → 8-bromo-3-methyl-N-(1-methylcyclopropyl)quinoxalin-2-amine

HRID 1055923Notes

Reaction equation

HRID 1055923 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5](F)[C:6]([CH3:12])=[N:7]2.Cl.[CH3:15][C:16]1([NH2:19])[CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:19][C:16]1([CH3:15])[CH2:18][CH2:17]1)[C:6]([CH3:12])=[N:7]2

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 12953687(1-Methylcyclopropyl)amine hydrochlorideHCID 897819405-Bromo-3-fluoro-2-methylquinoxaline

Product 1

HCID 897820988-bromo-3-methyl-N-(1-methylcyclopropyl)quinoxalin-2-amineYield 46%

Procedure

This compound (0.50 g, 45% yield) as a light yellow crystalline solid was prepared according to Example 174, using 5-bromo-3-fluoro-2-methylquinoxaline (126f; 0.96 g, 3.72 mmol), 1-methylcyclopropanamine hydrochloride (ChemBridge, San Diego, Calif.; 0.6 g, 5.58 mmol), and DIPEA (2.59 mL, 14.87 mmol) as starting materials: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.83 (dd, J=7.6, 1.2 Hz, 1H), 7.71 (dd, J=8.2, 1.2 Hz, 1H), 7.45-7.51 (m, 1H), 7.22 (t, J=7.8 Hz, 1H), 2.47 (s, 3H), 1.54 (s, 3H), 0.78-0.84 (m, 2H), 0.68-0.75 (m, 2H). m/z (ESI, +ve) 292/294 (M+H)+.

Sources & evidence

ORD record
ord-cbdb59eb2c9848dbb163116f66a74ac5
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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