2-Chloro-6-fluorobenzoic acid → 2-Chloro-N-[1-({5-chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-6-fluorobenzamide

To a solution of 2-chloro-6-fluorobenzoic acid (18 mg, 0.1 mmol, Aldrich) in DMF (0.1 ml) was added a solution of HATU (38 mg, 0.1 mmol) in DMF (0.2 ml). After 5 min, DIPEA (0.050 ml, 0.27 mmol) was added to the mixture. To the mixture was added a solution of 1-({5-chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-amine (for a preparation see Intermediate 55)(0.1 mmol) in DMF (0.1 ml). After shaking for 10 min, the resulting solution was allowed to stand for 16 h at ambient temperature. The solvent was removed using a genevac. The sample was dissolved in 1:1 MeOH:DMSO (0.6 ml) and purified by MDAP on a C18 column using Acetonitrile-Water with a TFA modifier (Method D). The solvent was evaporated in vacuo using the Genevac to give the title compound; LCMS (System 3) MH+=470/472, tRET=1.32 min.

1. waitto stand for 16 h at ambient temperature
2. customThe solvent was removed
3. dissolutionThe sample was dissolved in 1:1 MeOH
4. customDMSO (0.6 ml) and purified by MDAP on a C18 column
5. customThe solvent was evaporated in vacuo

ORD 기록

ord-f10750b87f584d34838e4fdeb69efe8a

출처 데이터셋

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08399436B2