Trifluoroacetic acid → HCID 18071055, compound

To a solution of 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (60 mg, 0.28 mmol) and diisopropylethylamine (49 mL, 0.28 mmol) in CH2Cl2 (2 mL) was added 2-fluorobenzenesulfonyl chloride (54 mg, 0.28 mmol) and the mixture was stirred at ambient temperature for 18 hr. To the resulting mixture was added trifluoroacetic acid (0.70 mL) and stirred at ambient temperature for 18 hr. The reaction mixture was concentrated and neutralized with saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the organic layer was concentrated to give 2-fluoro-N-piperidin-4-ylmethyl-benzenesulfonamide as a pale yellow solid. To a solution of above solid (0.076 g, 0.28 mmol) and diisopropylethylamine (0.072 mL, 0.42 mmol) in 2-propanol (3 mL) was added (2-chloro-quinazolin-4-yl)-dimethyl-amine obtained in step B of example 1 (0.044 g, 0.21 mmol) and the resulting mixture was stirred at 100° C. for 18 hr. The mixture was concentrated, and the residue was purified by column chromatography (silica gel, 5% MeOH in CH2Cl2) to give N-[1-(4-dimethylamino-quinazolin-2-yl)-piperidin-4-ylmethyl]-2-fluoro-benzenesulfonamide as a pale yellow solid (0.024 g, 26%).

1. stirringstirred at ambient temperature for 18 hr
2. concentrationThe reaction mixture was concentrated
3. extractionThe aqueous layer was extracted with EtOAc
4. concentrationthe organic layer was concentrated

ORD record

ord-c5c9d1fba7fe44b0a36c991fc9121e6c

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544690B2