Diisopropylethylamine → 2-(3-(3,3-dimethylmorpholino)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][O:28][CH2:27][CH2:26][NH:25]1.CCN(C(C)C)C(C)C>>[CH3:23][C:24]1([CH3:30])[N:25]([C:2]2[CH:3]=[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)[CH2:26][CH2:27][O:28][CH2:29]1Participants
Reactant 3
Product 1
Conditions
- Temperature
- 100 °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; 65 mg, 0.230 mmol), 3,3-dimethylmorpholine hydrochloride (69.8 mg, 0.461 mmol, Tyger Scientific, Ewing, N.J.), and DIPEA (201 μl, 1.151 mmol), heating at 100° C. for 3 h. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2-(3-(3,3-dimethylmorpholino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (12% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (s, 6H) 2.92 (t, J=6.85 Hz, 2H) 3.46-3.50 (m, 2H) 3.51 (s, 2H) 3.74-3.79 (m, 2H) 3.90-3.94 (m, 2H) 7.00 (br. s., 1H) 7.12 (d, J=2.15 Hz, 1H) 7.59 (t, J=7.82 Hz, 1H) 7.81 (dd, J=8.12, 1.27 Hz, 1H) 7.96 (dd, J=7.53, 1.27 Hz, 1H) 8.91 (s, 1H) 11.69 (br. s., 1H). MS (ESI, pos. ion) m/z: 378.0 (M+1).
Workup
- customPrepared similarly to that
- customPurification by silica gel (100% DCM to 4% MeOH/DCM)
Sources & evidence
- ORD record
- ord-5e6a582b4b184f1e99743b7657de3795
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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