Cyclobutylamine → HCID 136500837, compound

HRID 1056086Notes

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:21][C:15]3[N:16]=[CH:17][NH:18][C:19](=[O:20])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH:23]1([NH2:27])[CH2:26][CH2:25][CH2:24]1>CS(C)=O>[CH:23]1([NH:27][C:2]2[C:3]([CH3:22])=[N:4][C:5]3[C:10]([N:11]=2)=[C:9]([C:12]2[NH:21][C:15]4[N:16]=[CH:17][NH:18][C:19](=[O:20])[C:14]=4[CH:13]=2)[CH:8]=[CH:7][CH:6]=3)[CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 50 °C

Procedure

A glass microwave reaction vessel was charged with 6-(3-fluoro-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (Example 264; 60 mg, 0.203 mmol) and cyclobutylamine (0.173 mL, 2.032 mmol) in DMSO (0.6 mL). The reaction was heated in an oil bath at 50° C. for 15 min. The mixture was purified by rpHPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 5-40% ACN in water with 0.1% TFA). Product-containing fractions were combined and ACN was removed in vacuo. The residual mixture was neutralized with saturated aq. NaHCO3, and the suspension was filtered and dried to give 6-(3-(cyclobutylamino)-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (15 mg, 0.043 mmol, 21% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 347.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 12.69 (brs, 1H), 11.97 (brs, 1H), 8.10 (1H, d, J=7.2 Hz), 7.90 (1H, br. s.), 7.66 (1H, d, J=7.0 Hz), 7.47 (1H, br. s.), 7.37 (2H, br. s.), 4.50 (1H, br. s.), 2.58 (3H, br. s.), 2.16-2.28 (2H, m), 1.83-1.97 (2H, m).

Workup

customA glass microwave reaction vessel
customThe mixture was purified by rpHPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 5-40% ACN in water with 0.1% TFA)
customACN was removed in vacuo
filtrationthe suspension was filtered
customdried

Sources & evidence

ORD record: ord-c75f41f5afbf4e698f2593b0d7d793b1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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