Methoxyacetic Acid → HCID 11612589, compound

HATU (0.24 g) was added to a solution of N-(3-chloro-2-fluorophenyl)-6-methoxy-7-(piperidin-4-yloxy)quinazolin-4-amine dihydrochloride (250 mg), diisopropylethylamine (0.37 ml) and methoxyacetic acid (0.054 g) in methylene chloride (9 ml) and the mixture was stirred at room temperature for 2.5 hours. Methylene chloride (20 ml) was added and the organic layer was washed with aqueous sodium hydroxide (2M, 30 ml) and water (30 ml). The resulting product was purified by flash column chromatography eluting with methanol (3%) and methylene chloride (97%) to give a foam. This was re-precipitated by stirring in diethyl ether (20 ml) to give the title product as a white solid (0.200 g); 1H N Spectrum: (DMSO d6 373K) 1.73 (m, 2H), 2.02 (m, 2H), 3.37 (s, 3H), 3.41 (m, 2H), 3.77 (m, 2H), 3.98 (s, 3H), 4.09 (s, 2H), 4.85 (m, 1H), 7.26 (m, 1H), 7.30 (s, 1H), 7.39 (m, 1H), 7.59 (m, 1H), 7.81 (s, 1H), 8.38 (s, 1H), 9.34 (br s, 1H); Mass Spectrum: (M+H)+ 475.

1. washthe organic layer was washed with aqueous sodium hydroxide (2M, 30 ml) and water (30 ml)
2. customThe resulting product was purified by flash column chromatography
3. washeluting with methanol (3%) and methylene chloride (97%)
4. customto give a foam
5. customThis was re-precipitated
6. stirringby stirring in diethyl ether (20 ml)

ORD record

ord-e480d83f307d4033a152a4189eb8d05e

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569577B2