Diisopropylethylamine → 2-(2-methyl-3-((1-methylcyclobutyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1055964Notes

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.Cl.[CH3:24][C:25]1([NH2:29])[CH2:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C.CO.C(Cl)Cl>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:29][C:25]2([CH3:24])[CH2:28][CH2:27][CH2:26]2)=[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: 90 °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; 41.6 mg, 0.094 mmol), 1-methylcyclobutanamine hydrochloride (ChemBridge, San Diego, Calif.; 34.3 mg, 0.282 mmol), and DIPEA (0.098 mL, 0.564 mmol) in DMSO (0.8 mL), heating at 90° C. for 19 h. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(2-methyl-3-((1-methylcyclobutyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (26.4 mg, 0.073 mmol, 78% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.29 (1H, br. s.), 7.89 (1H, d, J=6.8 Hz), 7.56 (1H, d, J=7.2 Hz), 7.32 (1H, t, J=7.8 Hz), 7.04 (1H, d, J=1.8 Hz), 7.01 (1H, s), 6.98 (1H, br. s.), 3.45 (2H, td, J=6.8, 2.2 Hz), 2.92 (2H, t, J=6.7 Hz), 2.56 (3H, s), 2.42-2.49 (2H, m), 2.21-2.30 (2H, m), 1.86-2.00 (2H, m), 1.69 (3H, s). m/z (ESI, +ve) 362.3 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-91011455e9524969a50e62606912e056
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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