Triethylamine → HCID 9966038, Verbindung

Temperatur

80 °C

To a solution of 2-bromo-2-(2-tert-butoxycarbonylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone hydrobromide (synthesized from 2-(2-tert-butoxycarbonylamino-4-pyridyl)-1-(4-methoxyphenyl)ethanone (4.5 g, 13 mmol) according to the method described in Reference Example 20) in acetonitrile (40 mL) were added thiourea (1.1 g, 14 mmol) and triethylamine (1.9 mL, 14 mmol), and the mixture was stirred for 2 hours at 80° C. The reaction mixture was cooled to room temperature, then, concentrated. To the residue was added a saturated aqueous sodium hydrogen carbonate solution (200 mL), and the resulting solid was filtrated, and washed with water. To this solid was added 2N-hydrochloric acid (35 mL), and the mixture was stirred for 45 minutes at 100° C. The reaction mixture was cooled to room temperature, then, 8N-sodium hydroxide aqueous solution (10 mL) and aqueous sodium hydrogen carbonate solution (100 mL) were added. The resulted crude crystal was filtrated, and washed with water. This crude crystal was recrystallized from ethanol to obtain a title compound (2.7 g, yield 69%).

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationconcentrated
3. additionTo the residue was added a saturated aqueous sodium hydrogen carbonate solution (200 mL)
4. filtrationthe resulting solid was filtrated
5. washwashed with water
6. additionTo this solid was added 2N-hydrochloric acid (35 mL)
7. stirringthe mixture was stirred for 45 minutes at 100° C
8. temperatureThe reaction mixture was cooled to room temperature
9. addition8N-sodium hydroxide aqueous solution (10 mL) and aqueous sodium hydrogen carbonate solution (100 mL) were added
10. customThe resulted crude crystal
11. filtrationwas filtrated
12. washwashed with water
13. customThis crude crystal was recrystallized from ethanol

ORD-Eintrag

ord-68c77d6bed0a401c8ced56fddede4140

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07495018B2