Hydrochloric Acid → HCID 66744013, compound

Temperature

60 °C

To a solution of methyl 3-amino-5-bromothiophene-2-carboxylate (1.2 g, 5.08 mmol) in MeOH (15 mL) was added sodium hydroxide (0.61 g, 15.2 mmol) and water (5 mL). After stirring at 60° C. for 5 h, 6 M HCl (1.58 mL) was added to the mixture to adjust the pH to 10. After removal of the solvent at reduced pressure, the residue was dissolved in DMF (35 mL). Then, 1-hydroxybenzotriazole (4.1 g, 30.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.7 g, 30.5 mmol) and 4-methoxybenzyl amine (3.76 mL, 25.4 mmol) were added. After stirring at room temperature for 17 h, water was added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc) to give the title compound (1.46 g, 84%) as a yellow gum:

1. customAfter removal of the solvent at reduced pressure
2. dissolutionthe residue was dissolved in DMF (35 mL)
3. stirringAfter stirring at room temperature for 17 h
4. customto quench
5. customthe reaction
6. extractionThe organic materials were extracted with EtOAc
7. washThe combined extracts were washed with water and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customAfter removal of the solvent at reduced pressure
11. customthe residue was purified by column chromatography (Purif, silica gel, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc)

ORD record

ord-399cd99a28374d52b5d012a16d24d9e8

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691828B2