Hydrochloric Acid → HCID 66743876、化合物

温度

70 °C

Sodium hydroxide (4.27 g, 107 mmol) was dissolved with water (35 mL) and MeOH (140 mL). Then, methyl 5-bromo-4-methyl-3-(methylamino)thiophene-2-carboxylate (4.46 g, 16.7 mmol) was added to the mixture. The mixture was stirred at 70° C. overnight. After cooling in ice-water bath, 6 M HCl (11.9 mL, 71.4 mmol) was added, and the mixture was concentrated under reduced pressure. The residue was co-evaporated with toluene twice to give a yellow solid. This residue was mixed with ammonium chloride (38.1 g, 712 mmol), triethylamine (99 mL, 712 mmol) and DMF (300 mL), and the mixture was stirred for 5 min. Then, 1-hydroxybenzotriazole (32.7 g, 214 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (40.9 g, 214 mmol) were added to the mixture, and stirring was continued for 3 days. The reaction mixture was poured into saturated aqueous NaHCO3 (1 L). Extraction with EtOAc (1 L), washing with saturated NaHCO3, drying over MgSO4, filtration and concentration under reduced pressure gave a brown oil. This oil was purified by column chromatography (Purif, silica gel, hexane to EtOAc) to afford the title compound (2.34 g, 56%) as a brown oil:

1. concentrationthe mixture was concentrated under reduced pressure
2. customto give a yellow solid
3. stirringthe mixture was stirred for 5 min
4. stirringstirring
5. waitwas continued for 3 days
6. extractionExtraction with EtOAc (1 L)
7. washwashing with saturated NaHCO3
8. dry with materialdrying over MgSO4, filtration and concentration under reduced pressure
9. customgave a brown oil
10. customThis oil was purified by column chromatography (Purif, silica gel, hexane to EtOAc)

ORDレコード

ord-e566d65048e0472096a0cf4f999e212c

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08691828B2