N-Methylisopropylamine → HCID 89783957, compound

HRID 1055894Notes

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][NH:24][CH:25]([CH3:27])[CH3:26]>CS(C)=O>[CH3:22][C:3]1[C:2]([N:24]([CH3:23])[CH:25]([CH3:27])[CH3:26])=[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 according to Example 127, using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 40 mg, 0.135 mmol), N-methylpropan-2-amine (29.6 mg, 0.405 mmol, Sigma Aldrich), 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-(methyl(1-methylethyl)amino)-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one. 1H NMR (DMSO-d6) δ: 11.87 (br. s, 1H), 7.86-7.93 (m, 1H), 7.59-7.68 (m, 1H), 7.39-7.50 (m, 1H), 7.17 (s, 1H), 6.95 (br. s, 1H), 4.16-4.28 (m, 1H), 3.38-3.46 (m, 2H), 2.82-2.89 (m, 2H), 2.66 (s, 3H), 2.55 (s, 3H), 1.22-1.28 (m, 6H). m/z (ESI, +ve) 350.1 (M+H)+.

Workup

customPrepared
customPurification by
customhigh throughput parallel purification (Rilas Technologies, Woburn, Mass.)

Sources & evidence

ORD record: ord-b24fcacda8d34aeaa02e273c7d04673b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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