2-Butanamine, 2-methyl- → HCID 71731393, compound

HRID 1055971Notes

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]([NH2:28])([CH2:26][CH3:27])[CH3:25].CO.C(Cl)Cl>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:28][C:24]([CH2:26][CH3:27])([CH3:25])[CH3:23])=[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: 70 °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; 48.0 mg, 0.162 mmol) and 2-methylbutan-2-amine (Aldrich; 0.047 mL, 0.405 mmol) in DMSO (1.0 mL), heating 70° C. for 9 h. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(2-methyl-3-(tert-pentylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (30.5 mg, 0.084 mmol, 52% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.51 (1H, br. s.), 7.94 (1H, dd, J=7.5, 0.8 Hz), 7.65 (1H, dd, J=8.1, 0.7 Hz), 7.38 (1H, t, J=7.8 Hz), 7.11 (1H, d, J=2.0 Hz), 5.38 (1H, br. s.), 4.77 (1H, s), 3.66 (2H, td, J=6.8, 1.9 Hz), 2.99 (2H, t, J=6.8 Hz), 2.57 (3H, s), 2.03 (2H, q, J=7.4 Hz), 1.61 (6H, s), 0.97 (3H, t, J=7.4 Hz). m/z (ESI, +ve) 364.2 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-413b4b5bc1db432791e560fc12b572b6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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