Pyrrolidine → HCID 89783596, compound

HRID 1055962Notes

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.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.CO.C(Cl)Cl>CS(C)=O>[CH3:22][C:3]1[C:2]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]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: 85 °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; 41.3 mg, 0.098 mmol) and pyrrolidine (0.024 mL, 0.293 mmol) in DMSO (0.8 mL), heating at 85° C. for 40 min. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(2-methyl-3-(pyrrolidin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (21.0 mg, 0.060 mmol, 62% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.08 (1H, br. s.), 7.90 (1H, dd, J=7.4, 1.2 Hz), 7.58 (1H, dd, J=7.9, 1.1 Hz), 7.34 (1H, t, J=7.8 Hz), 7.11 (1H, d, J=2.2 Hz), 6.96 (1H, s), 3.71-3.85 (4H, m), 3.42 (2H, td, J=6.8, 2.3 Hz), 2.86 (2H, t, J=6.8 Hz), 2.79 (3H, s), 1.94-2.05 (4H, m). 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-6bf8976894b449b795696e4a62ba2417
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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