Diisopropylethylamine → 2-(3-(2,2-dimethylpiperidin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one
Reaction equation
F[C:2]1[CH:3]=[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.Cl.[CH3:23][C:24]1([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]1.CCN(C(C)C)C(C)C>>[CH3:23][C:24]1([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][N:25]1[C:2]1[CH:3]=[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]=2Participants
Reactant 3
Product 1
Conditions
- Temperature
- 120 °C
Procedure
Prepared similarly to that described in Example 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 110 mg, 0.390 mmol), 2,2-dimethylpiperidine hydrochloride (117 mg, 0.779 mmol, Anichem, North Brunswick, N.J.), and DIPEA (339 μl, 1.948 mmol), heating at 120° C. for 5 h. Purification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) provided 2-(3-(2,2-dimethylpiperidin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (14% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.48 (s, 6H) 1.61-1.82 (m, 6H) 2.87 (t, J=6.85 Hz, 2H) 3.45 (td, J=6.80, 2.45 Hz, 2H) 3.61-3.66 (m, 2H) 6.96 (br. s., 1H) 7.09 (d, J=2.35 Hz, 1H) 7.52 (t, J=7.82 Hz, 1H) 7.73 (dd, J=8.12, 1.27 Hz, 1H) 7.93 (dd, J=7.43, 1.37 Hz, 1H) 8.78 (s, 1H) 11.76 (br. s., 1H). MS (ESI, pos. ion) m/z: 376.3 (M+1).
Workup
- customPrepared similarly to that
- customPurification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA)
Sources & evidence
- ORD record
- ord-26201ad9e6ef4945ae10c43695d847b6
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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