Hydrochloric Acid → HCID 59006336, compound

Tert-butyl 4-(1-hydroxy-3-methoxy-3-oxo-1-(3-pivalamidothiophen-2-yl)propan-2-yl)piperidine-1-carboxylate (10 g, 21.34 mmol) was dissolved in MeOH (20 mL), water (20.00 ml), hydrochloric acid (concentrated, 20 ml, 244 mmol), the resulting red pink solution was heated, the color changed to dark tan, and the mixture was refluxed in a oil bath under N2 over night, conversion was completed as determined by LC/MS. Most of the solvent was removed on rotary vacuo, the resulting gum type residue was triturate with EtOAc/MeOH (10 mL/2 mL), filtered and washed with EtOAC/MeOH (10 mL/1 mL) to afford the expected product, 6-(piperidin-4-yl)thieno[3,2-b]pyridin-5(4H)-one (4.85 g, 97%), as a brown solid. 1H-NMR (400 MHz, MeOD) δ ppm 1.83-1.94 (m, J=13.41, 13.13, 13.13, 3.90 Hz, 2 H) 2.13 (d, J=13.85 Hz, 2 H) 3.08-3.19 (m, 4 H) 3.50 (dd, J=10.58, 2.01 Hz, 2 H) 7.08 (d, J=6.04 Hz, 1 H) 7.78 (d, J=5.54 Hz, 1 H) 7.96 (s, 1 H); Mass spec. 235.16 (MH+), Calc. for C12H14N2OS 234.08.

1. temperaturethe mixture was refluxed in a oil bath under N2 over night
2. customMost of the solvent was removed on rotary vacuo
3. customthe resulting gum type residue was triturate with EtOAc/MeOH (10 mL/2 mL)
4. filtrationfiltered
5. washwashed with EtOAC/MeOH (10 mL/1 mL)

ORD record

ord-366e632f981d4601946784f0fef618aa

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470680B2