Diisopropylethylamine → 2-(3-((2-methoxy-1,1-dimethylethyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 1055890Notes

Reaction equation

CCN(C(C)C)C(C)C.Cl.[CH3:11][O:12][CH2:13][C:14]([NH2:17])([CH3:16])[CH3:15].F[C:19]1[C:20]([CH3:39])=[N:21][C:22]2[C:27]([N:28]=1)=[C:26]([C:29]1[NH:37][C:36]3[CH2:35][CH2:34][NH:33][C:32](=[O:38])[C:31]=3[CH:30]=1)[CH:25]=[CH:24][CH:23]=2>CS(C)=O>[CH3:11][O:12][CH2:13][C:14]([NH:17][C:19]1[C:20]([CH3:39])=[N:21][C:22]2[C:27]([N:28]=1)=[C:26]([C:29]1[NH:37][C:36]3[CH2:35][CH2:34][NH:33][C:32](=[O:38])[C:31]=3[CH:30]=1)[CH:25]=[CH:24][CH:23]=2)([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

Prepared according to Example 127, using DIPEA (264 μl, 1.519 mmol), (2-methoxy-1,1-dimethylethyl)amine hydrochloride (78 mg, 0.759 mmol, ChemBridge Corp., San Diego, Calif.), 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 75 mg, 0.253 mmol), and DMSO (2.2 mL) and stirring at 100° C. for 3 h. Purification by reverse phase HPLC (Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in ACN/H2O, gradient 5% to 80%) provided 2-(3-((2-methoxy-1,1-dimethylethyl)amino)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (27 mg, 28.1%). 1H NMR (DMSO-d6) δ: 11.83-11.94 (m, 1H), 7.77-7.83 (m, 1H), 7.56-7.62 (m, 1H), 7.31-7.39 (m, 1H), 6.90-6.98 (m, 1H), 5.87-5.92 (m, 1H), 3.62-3.68 (m, 2H), 3.40-3.46 (m, 1H), 3.16-3.20 (m, 2H), 2.81-2.88 (m, 2H), 2.66-2.69 (m, 2H), 2.31-2.36 (m, 3H), 1.50-1.56 (m, 6H). m/z (ESI, +ve) 380.1 (M+H)+.

Workup

customPrepared
customPurification by reverse phase HPLC (Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in ACN/H2O, gradient 5% to 80%)

Sources & evidence

ORD record: ord-fb42b76649574c8c9f9560f6704537fb
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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