Water → HCID 178432142, compound

HRID 1056322Notes

Reaction equation

[NH2:1][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.CCN(C(C)C)C(C)C.Cl.[NH2:33][C:34](N)=[NH:35].O>CS(C)=O>[CH3:22][C:3]1[C:2]([NH:1][C:34]([NH2:35])=[NH:33])=[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: 70 °C

Procedure

A mixture of 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (445a, 10 mg, 0.33 mmol), DIEA (0.29 mL, 1.68 mmol), and guanidine hydrochloride (0.025 mL, 0.37 mmol) in DMSO (3 mL) was stirred at 70° C. for 24 h. The reaction mixture was cooled, H2O was added, and extracted with DCM (3×). The extracts were dried over Na2SO4, concentrated and purified by reverse phase HPLC. The pure fractions were concentrated, dissolved in MeOH, and neutralized by Stratosphere SPE (PL-HCO3 MP-resin) to give the title compound (12 mg, 11%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.73 (1H, br. s.), 9.95 (1H, br. s.), 8.53-8.39 (3H, br. s.), 7.84 (1H, br. s.), 7.73 (1H, br. s.), 7.02 (1H, br. s.), 6.77 (1H, s), 3.38-3.52 (2H, t, J=6.8 Hz), 2.87 (2H, t, J=6.8 Hz), 2.73 (3H, s). m/z (ESI, +ve) 336 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
extractionextracted with DCM (3×)
dry with materialThe extracts were dried over Na2SO4
concentrationconcentrated
custompurified by reverse phase HPLC
concentrationThe pure fractions were concentrated
dissolutiondissolved in MeOH

Sources & evidence

ORD record: ord-66567e61c680475787b966e515db18c5
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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