Diisopropylethylamine → HCID 89784433, compound

HRID 1055961Notes

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.Cl.[CH3:24][O:25][C:26](=[O:30])[C@@H:27]([CH3:29])[NH2:28].CCN(C(C)C)C(C)C.CO.C(Cl)Cl>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:28][C@H:27]([CH3:29])[C:26]([O:25][CH3:24])=[O:30])=[N:11][C:10]2[C:5]([N:4]=1)=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]1[NH:20][C:19]2[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=2[CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Prepared similar to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 37.7 mg, 0.089 mmol), D-alanine methyl ester hydrochloride (Aldrich; 37.3 mg, 0.267 mmol), and DIPEA (0.093 mL, 0.534 mmol) in DMSO (0.8 mL), heating at 100° C. for 30 min. Chromatographic purification (silica gel, 0-100% EtOAc/hexanes, then 0-10% MeOH/DCM) furnished (R)-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 (21.3 mg, 0.056 mmol, 63% yield) as a yellow-orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.57 (1H, br. s.), 7.87 (1H, dd, J=7.5, 1.1 Hz), 7.58 (1H, dd, J=7.9, 1.1 Hz), 7.44 (1H, d, J=6.7 Hz), 7.34 (1H, t, J=7.8 Hz), 6.94 (1H, s), 6.89 (1H, d, J=2.2 Hz), 4.72 (1H, quin, J=7.1 Hz), 3.50 (3H, s), 3.42 (2H, td, J=6.7, 2.2 Hz), 2.91 (2H, td, J=6.8, 2.8 Hz), 2.59 (3H, s), 1.57 (3H, d, J=7.2 Hz). m/z (ESI, +ve) 380.3 (M+H)+.

Workup

customPrepared similar to
customChromatographic purification (silica gel, 0-100% EtOAc/hexanes

Sources & evidence

ORD record: ord-07c3992881c74571803ef3067f821217
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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