Sodium hydride → HCID 11330771, compound

Temperature

60 °C

Sodium hydride (8 mg, 0.366 mmol) was added to a solution of N-hydroxy-2-phenyl-acetamidine (50 mg, 0.366 mmol) in tetrahydrofuran (15 mL). The solution was stirred at 60° C. for 15 min. A solution of (±)-3-(7-methyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester (60 mg, 0.122 mmol) in tetrahydrofuran (5 mL) was added. The reaction mixture was stirred at 60° C. for 18 h. The reaction was then cooled to room temperature and the solvent removed under reduced pressure. The residue was dissolved with methylene chloride and partitioned with water and extracted with methylene chloride (3×50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduce pressure. Purification was carried out by preparative HPLC. LC/MS: tR=1.79 min, 591 (MH)+.

1. stirringThe reaction mixture was stirred at 60° C. for 18 h
2. temperatureThe reaction was then cooled to room temperature
3. customthe solvent removed under reduced pressure
4. dissolutionThe residue was dissolved with methylene chloride
5. custompartitioned with water
6. extractionextracted with methylene chloride (3×50 mL)
7. dry with materialThe organic layer was dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customPurification

ORD record

ord-af719b5dd8474015a7cc1213c65504e2

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569578B2