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

HRID 1055896Notes

Reaction equation

FC1C(C)=NC2C(N=1)=C([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)C=CC=2.CC(N)(C)CN>CS(C)=O>[NH:20]1[C:19]2[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=2[CH:13]=[CH:12]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), 2-methylpropane-1,2-diamine (35.7 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-(34(2-amino-2-methylpropyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one. 1H NMR (DMSO-d6) δ: 12.79-12.88 (m, 1H), 7.82-7.88 (m, 1H), 7.52-7.57 (m, 1H), 7.25-7.32 (m, 1H), 7.11-7.23 (m, 1H), 6.96-7.01 (m, 1H), 6.89-6.95 (m, 1H), 4.31-4.37 (m, 1H), 3.44-3.48 (m, 5H), 2.91-2.97 (m, 2H), 2.54-2.60 (m, 3H), 1.20 (s, 6H). m/z (ESI, +ve) 365.1 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-f31da3998d284e2aad9c7100a0abced3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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