Diisopropylethylamine → methyl 2-methyl-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)propanoate

HRID 1055887Notes

Reaction equation

CCN(C(C)C)C(C)C.Cl.[CH3:11][O:12][C:13](=[O:18])[C:14]([NH2:17])([CH3:16])[CH3:15].F[C:20]1[C:21]([CH3:40])=[N:22][C:23]2[C:28]([N:29]=1)=[C:27]([C:30]1[NH:38][C:37]3[CH2:36][CH2:35][NH:34][C:33](=[O:39])[C:32]=3[CH:31]=1)[CH:26]=[CH:25][CH:24]=2>CS(C)=O>[CH3:15][C:14]([NH:17][C:20]1[C:21]([CH3:40])=[N:22][C:23]2[C:28](=[C:27]([C:30]3[NH:38][C:37]4[CH2:36][CH2:35][NH:34][C:33](=[O:39])[C:32]=4[CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[N:29]=1)([CH3:16])[C:13]([O:12][CH3:11])=[O:18]

Participants

Conditions

Temperature: 95 °C

Procedure

Prepared according to Example 131, using DIPEA (1761 μl, 10.12 mmol), aminoisobutyric acid methyl ester hydrochloride (778 mg, 5.06 mmol, Sigma Aldrich), and 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 500 mg, 1.687 mmol) in DMSO (8437 μl) stirring at 95° C. for 2 h. Purification by column chromatography (silica gel: 0 to 10% MeOH/DCM) provided methyl 2-methyl-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)propanoate (557 mg, 81%). 1H NMR (CDCl3) δ: 11.16-11.25 (m, 1H), 7.96-8.01 (m, 1H), 7.69-7.74 (m, 1H), 7.40-7.46 (m, 1H), 7.08-7.12 (m, 1H), 5.56-5.71 (m, 1H), 5.15-5.20 (m, 1H), 3.66-3.73 (m, 2H), 3.56 (s, 3H), 3.25 (s, 2H), 2.65 (s, 3H), 1.79 (s, 6H). m/z (ESI, +ve) 394.1 (M+H)+.

Workup

customPrepared
customPurification by column chromatography (silica gel: 0 to 10% MeOH/DCM)

Sources & evidence

ORD record: ord-2f3211bb948d41bc969f7e1aeb206e48
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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