N-tert-Butylethylamine → 2-(3-(tert-butyl(ethyl)amino)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.[CH2:22]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:23]>>[C:25]([N:24]([CH2:22][CH3:23])[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)([CH3:28])([CH3:27])[CH3:26]Participants
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; 79 mg, 0.280 mmol) and N-ethyl-2-methylpropan-2-amine (142 mg, 1.399 mmol, TCI International, Portland, Oreg.), heating at 120° C. for 16 h. Purification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10100% ACN/water with 0.1% TFA) provided 2-(3-(tert-butyl(ethyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (16% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (t, J=6.94 Hz, 3H) 1.60 (s, 9H) 2.85 (t, J=6.94 Hz, 2H) 3.43 (td, J=6.80, 2.25 Hz, 2H) 3.80 (q, J=6.91 Hz, 2H) 6.94 (br. s., 1H) 7.03 (d, J=2.15 Hz, 1H) 7.41 (t, J=7.73 Hz, 1H) 7.69 (d, J=8.22 Hz, 1H) 7.87 (d, J=7.43 Hz, 1H) 8.71 (s, 1H) 11.69 (br. s., 1H). MS (ESI, pos. ion) m/z: 364.1 (M+1).
Workup
- customPrepared similarly to that
- customPurification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10100% ACN/water with 0.1% TFA)
Sources & evidence
- ORD record
- ord-ed70da3941644497b2f05ffa22fbbf7b
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Reaction notes
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