1,2-Dimethylpropylamine → HCID 89783661, compound

HRID 1055898Notes

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][CH:24]([CH3:28])[CH:25]([NH2:27])[CH3:26]>CS(C)=O>[CH3:26][CH:25]([NH:27][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)[CH:24]([CH3:28])[CH3:23]

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), rac-3-methylbutan-2-amine (35.3 mg, 0.405 mmol, Sigma Aldrich), and DMSO (1.4 mL) stirring at 80° C. for 2 h. Purification by high throughput parallel purification (Rilas Technologies, Woburn, Mass.) provided 2-(3-(((±)-1,2-dimethylpropyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one. 1H NMR (DMSO-d6) δ: 11.95-12.11 (m, 1H), 7.81-7.91 (m, 1H), 7.49-7.67 (m, 1H), 7.26-7.37 (m, 1H), 7.08-7.21 (m, 1H), 6.86-7.02 (m, 1H), 6.65-6.84 (m, 1H), 4.01-4.20 (m, 1H), 3.38-3.50 (m, 2H), 2.84-2.96 (m, 2H), 2.58 (s, 3H), 1.98-2.13 (m, 1H), 1.21-1.34 (m, 3H), 0.93-1.12 (m, 6H). m/z (ESI, +ve) 364.1 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-1babfaa2f0dd4478a7709c5f71d219a5
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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