Azetidine → HCID 89784458, compound

HRID 1055963Notes

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

Participants

Conditions

Temperature: 60 °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; 38.0 mg, 0.090 mmol) and azetidine (Aldrich; 0.018 mL, 0.269 mmol) in DMSO (0.8 mL), heating at 60° C. for 40 min. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(3-(azetidin-1-yl)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (13.3 mg, 0.040 mmol, 44% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.05 (1H, br. s.), 7.91 (1H, dd, J=7.5, 1.1 Hz), 7.59 (1H, dd, J=7.8, 1.0 Hz), 7.36 (1H, t, J=7.7 Hz), 7.14 (1H, d, J=2.2 Hz), 6.96 (1H, s), 4.41 (4H, t, J=7.6 Hz), 3.42 (2H, td, J=6.6, 2.1 Hz), 2.87 (2H, t, J=7.0 Hz), 2.60 (3H, s), 2.35-2.45 (2H, m). m/z (ESI, +ve) 334.1 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-eb7b56aae1414397bd384aee032bc7cb
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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