Cyclopropylamine → 8-bromo-N-cyclopropyl-3-methylquinoxalin-2-amine

HRID 1056059Notes

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.[CH:14]1([NH2:17])[CH2:16][CH2:15]1>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:17][CH:14]1[CH2:16][CH2:15]1)[C:6]([CH3:12])=[N:7]2

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 897819405-Bromo-3-fluoro-2-methylquinoxaline

Product 1

HCID 897823468-bromo-N-cyclopropyl-3-methylquinoxalin-2-amineYield 83%

Procedure

This compound (1.06 g, 83% yield) as a light yellow crystalline solid was prepared similarly to that described in the preparation of Example 174a, using 5-bromo-3-fluoro-2-methylquinoxaline (Example 126f; 1.11 g, 4.60 mmol) and cyclopropanamine (Aldrich; 1.50 mL, 21.65 mmol) as starting materials. 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (1H, dd, J=7.6, 1.2 Hz), 7.78 (1H, dd, J=8.2, 1.2 Hz), 7.19-7.26 (1H, m), 5.12 (1H, br. s.), 3.04-3.14 (1H, m), 2.47-2.55 (3H, m), 0.93-1.01 (2H, m), 0.60-0.68 (2H, m). m/z (ESI, +ve) 278/280 (M+H)+.

Workup

customthat described in the preparation of Example 174a

Sources & evidence

ORD record: ord-09239c8be5c8444f84be721e21e3de61
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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