1-Methylazetidin-3-amine → 2-(2-methyl-3-((1-methyl-3-azetidinyl)amino)-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 1056070Notes

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.[CH3:23][N:24]1[CH2:27][CH:26]([NH2:28])[CH2:25]1>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:28][CH:26]2[CH2:27][N:24]([CH3:23])[CH2:25]2)=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=2)[N:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Prepared similarly to that described in Example 127, using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 75 mg, 0.135 mmol), 1-methylazetidin-3-amine (87 mg, 0.405 mmol), and DMSO (1.4 mL) and stirring at 80° C. for 2 h. Purification by high-throughput parallel purification (Rilas Technologies, Woburn, Mass.) provided 2-(2-methyl-3-((1-methyl-3-azetidinyl)amino)-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one. 1H NMR (MeOH-d4) δ: 7.80-7.85 (m, 1H), 7.63-7.68 (m, 1H), 7.36-7.42 (m, 1H), 6.93 (s, 1H), 3.59-3.65 (m, 2H), 3.22-3.26 (m, 2H), 3.11-3.14 (m, 1H), 2.97-3.04 (m, 2H), 2.59 (s, 3H), 2.01 (s, 3H). m/z (ESI, +ve) 363.2 (M+H)+.

Workup

customPrepared similarly to
customPurification
customby high-throughput parallel purification (Rilas Technologies, Woburn, Mass.)

Sources & evidence

ORD record: ord-ab30530713f349a6adf2cf8471ffb9ec
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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