Butylamine → HCID 89784354, compound

HRID 1055973Notes

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.[CH2:23]([NH2:27])[CH2:24][CH2:25][CH3:26].CO.C(Cl)Cl>CS(C)=O>[CH2:23]([NH:27][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)[CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 75 °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; 41.5 mg, 0.140 mmol) and butan-1-amine (0.042 mL, 0.420 mmol) in DMSO (1.0 mL), heating at 75° C. for 45 min. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished 2-(3-(butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (6.28 mg, 0.018 mmol, 13% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.15 (1H, br. s.), 7.88 (1H, d, J=7.4 Hz), 7.56 (1H, d, J=8.0 Hz), 7.27-7.36 (2H, m), 7.13 (1H, d, J=1.6 Hz), 6.94 (1H, br. s.), 3.52 (2H, q, J=6.7 Hz), 3.44 (2H, td, J=6.7, 2.0 Hz), 2.87 (2H, t, J=6.7 Hz), 2.53 (3H, s), 1.72 (2H, quin, J=7.4 Hz), 1.47 (2H, sxt, J=7.3 Hz), 0.94 (3H, t, J=7.3 Hz). m/z (ESI, +ve) 350.1 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-01d79ec1f94549dbabb880fe2892cc47
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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