Diisopropylethylamine → 1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one

HRID 1055893Notes

Reaction equation

CCN(C(C)C)C(C)C.FC1C(C)=NC2C(N=1)=C([C:21]1[NH:29][C:28]3[CH2:27][CH2:26][NH:25][C:24](=[O:30])[C:23]=3[CH:22]=1)C=CC=2.CC1(N)CCCC1>CS(C)=O>[NH:29]1[C:28]2[CH2:27][CH2:26][NH:25][C:24](=[O:30])[C:23]=2[CH:22]=[CH:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

Prepared according to Example 127, using DIPEA (141 μl, 0.803 mmol), 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), 1-methylcyclopentanamine (40.2 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-(1-methylcyclopentyl)amino)-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one. 1H NMR (DMSO-d6) δ: 12.21 (s, 1H), 7.83-7.91 (m, 1H), 7.53-7.61 (m, 1H), 7.30-7.39 (m, 1H), 7.07 (s, 1H), 6.95 (s, 1H), 6.18 (s, 1H), 3.40-3.48 (m, 2H), 2.85-2.94 (m, 2H), 2.55 (s, 3H), 2.37-2.48 (m, 2H), 1.67-1.85 (m, 6H), 1.64 (s, 3H). m/z (ESI, +ve) 376.1 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-05c7373701ea4abeab7c68fa6d79b620
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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