Benzofuran-2-carboxylic acid → HCID 22141240, compound

To a solution of 1-benzofuran-2-carboxylic acid (201 mg, 1.24 mmol) in N,N-dimethylformamide (25 ml) was added 1-hydroxybenzotriazole monohydrate (200 mg, 1.31 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (340 mg, 1.77 mmol). After stirring at room temperature for 10 min the mixture was treated with the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 400 mg, 1.3 mmol) and sodium hydrogen carbonate (220 mg, 2.6 mmol). The reaction mixture was stirred at room temperature overnight before concentrating in vacuo. Water (15 ml) was added and the reaction mixture was extracted with ethyl acetate (2×20 ml). The combined organic extracts were treated with water (15 ml) upon which a buff solid precipitated. The biphasic mixture was filtered to afford 380 mg of a buff solid. The biphasic filtrate was separated and the organic layer was dried (MgSO4), and concentrated in vacuo to afford a further 80 mg of buff solid. The combined buff solid was warmed to 60° C. in methanol and allowed to slowly cool to room temperature upon which the title compound was collected by filtration as an off-white solid (340 mg, 63%).

1. stirringThe reaction mixture was stirred at room temperature overnight
2. concentrationbefore concentrating in vacuo
3. additionWater (15 ml) was added
4. extractionthe reaction mixture was extracted with ethyl acetate (2×20 ml)
5. additionThe combined organic extracts were treated with water (15 ml) upon which a buff solid
6. customprecipitated
7. filtrationThe biphasic mixture was filtered
8. customto afford 380 mg of a buff solid
9. customThe biphasic filtrate was separated
10. dry with materialthe organic layer was dried (MgSO4)
11. concentrationconcentrated in vacuo
12. customto afford a further 80 mg of buff solid

ORD record

ord-60543c4919024ea08ed3668dc5090054

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049444B2