Hydrochloric Acid → HCID 178503626, compound

HRID 589994Notes

Reaction equation

[CH3:1][S:2][C:3]1[S:4][C:5]([C:19]2[CH:23]=[CH:22][N:21](COCC[Si](C)(C)C)[N:20]=2)=[C:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8](=[O:18])[C:7]=12.Cl>CO>[CH3:1][S:2][C:3]1[S:4][C:5]([C:19]2[CH:23]=[CH:22][NH:21][N:20]=2)=[C:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:8](=[O:18])[C:7]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(methylsulfanyl)-5-phenyl-1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridin-4(5H)-one (45 mg, 0.095 mmol) in MeOH (25 μL) at rt was added 4M HCl in MeOH (25 μL, 0.095 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 as a mixture of amide rotamers. 1H NMR (400 MHz, ppm, CDCl3) δ 7.62 (d, J=2.4 Hz, 1 H); 7.45-7.30 (m, 4 H); 7.28-7.22 (m, 1 H); 6.42 (d, J=2.4 Hz, 1 H); 3.96 (t, J=6.3 Hz, 2 H); 3.23 (t, J=6.3 Hz, 3 H); 2.62 (s, 3 H). HRMS (ES+) m/z 342.0728 [(M+H)+; calcd for C17H15N3OS2: 342.0729].

Workup

concentrationThe resulting mixture was concentrated
custompurified by Gilson reverse phase chromatography

Sources & evidence

ORD record: ord-6660ab0823974f9383b29b3ae18d3734
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233977B2

Reaction notes

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