2-Methylallylamine → HCID 89784464, compound

HRID 1055960Notes

Reaction equation

F[C:2]1[C:3]([CH3:22])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH3:23][C:24](=[CH2:27])[CH2:25][NH2:26].CO.C(Cl)Cl>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:26][CH2:25][C:24]([CH3:27])=[CH2:23])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=2)[N:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Prepared similar to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 45.5 mg, 0.107 mmol) and 2-methylallylamine (Matrix Scientific, Columbia, S.C.; 0.039 mL, 0.430 mmol) in DMSO (0.8 mL), heating at 80° C. for 30 min. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(2-methyl-3-((2-methylallyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (22.0 mg, 0.063 mmol, 59% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.83 (1H, br. s.), 7.87 (1H, dd, J=7.6, 1.2 Hz), 7.59 (1H, t, J=5.6 Hz), 7.56 (1H, m, J=8.0, 1.2 Hz), 7.31 (1H, t, J=7.8 Hz), 7.10 (1H, d, J=2.2 Hz), 6.93 (1H, s), 4.86 (1H, s), 4.83 (1H, s), 4.05 (2H, d, J=5.7 Hz), 3.42 (2H, td, J=6.8, 2.3 Hz), 2.86 (2H, t, J=6.8 Hz), 2.57 (3H, s), 1.85 (3H, s). m/z (ESI, +ve) 348.2 (M+H)+.

Workup

customPrepared similar to
customChromatographic purification (silica gel, 0-100% EtOAc/hexanes

Sources & evidence

ORD record: ord-76ec84f21cf74218ba3102df45767de6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

Loading…