Hydrochloric Acid → HCID 66743363, compound

Temperature

70 °C

A mixture of 3 M sodium hydroxide (2.5 mL, 7.50 mmol), MeOH (10 mL) and methyl 5-bromo-3-(methylamino)thiophene-2-carboxylate (674 mg, 2.69 mmol) was stirred at 70° C. overnight. Then, the mixture was cooled in ice-water bath, and 6 M HCl (0.9 mL, 5.40 mmol) was added. The mixture was concentrated under reduced pressure to give a yellow solid. This residue was mixed with ammonium chloride (2.88 g, 53.9 mmol), triethylamine (7.51 mL, 53.9 mmol) and DMF (27 mL). The mixture was stirred for 5 min, then 1-hydroxybenzotriazole (2.19 g, 16.2 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (3.10 g, 16.2 mmol) were added. The stirring was continued for 3 days. The reaction mixture was poured into saturated aqueous NaHCO3 (200 mL). Extraction with EtOAc (200 mL), washing with saturated NaHCO3, drying over MgSO4, filtration and concentration under reduced pressure gave brown oil. This oil was purified by column chromatography (Purif, silica gel, hexane to EtOAc) to afford the title compound (536 mg, 85%) as a pale brown solid:

1. concentrationThe mixture was concentrated under reduced pressure
2. customto give a yellow solid
3. stirringThe mixture was stirred for 5 min
4. waitThe stirring was continued for 3 days
5. extractionExtraction with EtOAc (200 mL)
6. washwashing with saturated NaHCO3
7. dry with materialdrying over MgSO4, filtration and concentration under reduced pressure
8. customgave brown oil
9. customThis oil was purified by column chromatography (Purif, silica gel, hexane to EtOAc)

ORD record

ord-2dfe5edf47da4f22b8ce1f4ea5a5a510

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691828B2