1-Methyl-2-pyrrolecarboxylic acid → HCID 58157688, compound

A solution of N-methylpyrrole-2-carboxylic acid (12.5 mg, 0.1 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.048 g, 0.11 mmol) and N,N-diisopropylethylamine (52.2 μL, 0.3 mmol) in N,N-dimethylformamide (1 mL, 12.9 mmol) was stirred at room temperature for 15 minutes. A solution of ethyl 3-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (22.5 mg, 0.1 mmol) in N,N-dimethylformamide (1 mL) was then added and the reaction was further stirred at room temperature overnight. The solution was evaporated to dryness and the residue obtained was partitioned between DCM (2 mL) and half-saturated aqueous sodium bicarbonate solution (2 mL). Upon separation of the layers, the aqueous layer was extracted with additional DCM (2 mL) and the combined organic layers were concentrated to dryness.

1. customThe solution was evaporated to dryness
2. customthe residue obtained
3. customwas partitioned between DCM (2 mL) and half-saturated aqueous sodium bicarbonate solution (2 mL)
4. customUpon separation of the layers
5. extractionthe aqueous layer was extracted with additional DCM (2 mL)
6. concentrationthe combined organic layers were concentrated to dryness

ORD record

ord-595794b9442749f6afdba6ef3c09cee5

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08624040B2