Cycloheptylamine → HCID 89783766, compound

HRID 1055959Notes

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([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CO.C(Cl)Cl>CS(C)=O>[CH:23]1([NH:30][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)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 100 °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; 38.7 mg, 0.091 mmol) and cycloheptanamine (TCI America, Portland, Oreg.; 0.035 mL, 0.274 mmol) in DMSO (0.8 mL), heating at 100° C. for 40 min. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(3-(cycloheptylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (29.8 mg, 0.077 mmol, 84% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.95 (1H, br. s.), 7.86 (1H, d, J=7.6 Hz), 7.55 (1H, d, J=7.8 Hz), 7.30 (1H, t, J=7.8 Hz), 7.11 (1H, d, J=2.0 Hz), 6.92 (1H, br. s.), 6.79 (1H, d, J=7.4 Hz), 4.14-4.29 (1H, m), 3.44 (2H, td, J=6.8, 2.2 Hz), 2.88 (2H, t, J=6.7 Hz), 2.53 (3H, br. s.), 1.97-2.10 (2H, m), 1.62-1.79 (6H, m), 1.49-1.61 (4H, m). m/z (ESI, +ve) 390.2 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-22dd8ad877ec4b36af883a1b983f8198
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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