Cyclopentylamine → HCID 89783764, compound

HRID 1055957Notes

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.[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1.CO.C(Cl)Cl>CS(C)=O>[CH:23]1([NH:28][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)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 100 °C

Procedure

Prepared according to Example 127 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 39.8 mg, 0.094 mmol) and cyclopentanamine (0.028 mL, 0.282 mmol) in DMSO (0.8 mL), heating at 100° C. for 50 min. Purification by reversed-phase HPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA) followed by chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-3% MeOH/DCM) furnished 2-(3-(cyclopentylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (6.8 mg, 0.019 mmol, 20% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.27 (1H, br. s.), 7.89 (1H, d, J=7.4 Hz), 7.56 (1H, d, J=7.6 Hz), 7.32 (1H, t, J=7.8 Hz), 7.12 (1H, s), 6.94 (1H, d, J=5.9 Hz), 4.34-4.42 (1H, m), 4.03 (1H, s), 3.43 (2H, t, J=6.9 Hz), 2.87 (2H, t, J=6.8 Hz), 2.55 (3H, s), 2.04-2.17 (2H, m), 1.69-1.83 (4H, m), 1.66 (2H, d, J=7.6 Hz). m/z (ESI, +ve) 362.1 (M+H)+.

Workup

customPrepared
customPurification by reversed-phase HPLC (Phenomenex Gemini C18 column (150×30 mm, 10 μm), 35 mL/min, 5-100% ACN/H2O+0.1% TFA)
customfollowed by chromatographic purification (silica gel, 0-100% EtOAc/hexanes

Sources & evidence

ORD record: ord-7b08a729713d4361a326a70ee90051e3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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