Hydrochloric Acid → HCID 178503628, compound

HRID 589992Notes

Reaction equation

[CH3:1][S:2][C:3]1[S:4][C:5]([C:16]2[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[N:17]=2)=[C:6]2[CH2:11][CH2:10][N:9]([CH:12]([CH3:14])[CH3:13])[C:8](=[O:15])[C:7]=12.Cl>CO>[CH3:1][S:2][C:3]1[S:4][C:5]([C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)=[C:6]2[CH2:11][CH2:10][N:9]([CH:12]([CH3:14])[CH3:13])[C:8](=[O:15])[C:7]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(methylsulfanyl)-5-(propan-2-yl)-1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridin-4(5H)-one (45 mg, 0.10 mmol) in MeOH (26 μL) at rt was added 4M HCl in MeOH (26 μL, 0.10 mmol). The solution was heated at 80° C. for 1 h. The resulting mixture was concentrated and purified by Gilson reverse phase chromatography to afford the title compound. 1H NMR (400 MHz, ppm, CDCl3) 7.60 (d, J=2.4 Hz, 1 H); 6.38 (d, J=2.4 Hz, 1 H); 5.00 (sep, J=6.8 Hz, 1 H); 3.40 (t, J=6.4 Hz, 2 H); 3.03 (t, J=6.4 Hz, 21-1); 2.60 (s, 3 H); 1.20 (s, 3 H); 1.18 (s, 3 H). HRMS (ES+) m/z 308.0884 [(M+H)+; calcd for C14H17N3OS2: 308.0886].

Workup

concentrationThe resulting mixture was concentrated
custompurified by Gilson reverse phase chromatography

Sources & evidence

ORD record: ord-f3a1857bb61e4455885fec418cc09d46
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233977B2

Reaction notes

Loading…