4-Chloro-N-methylbenzenamine → 4-(3-{4-[(4-Chloro-phenyl)-methyl-carbamoyl]-2-fluoro-phenoxy}-propyl)-piperazine-1-carboxylic Acid Tert-butyl Ester

PyBroP (606 mg, 1.3 mmol) was added to a solution of 4-[3-(4-carboxy-2-fluoro-phenoxy)-propyl]-piperazine-1-carboxylic acid tert-butyl ester from Example E39 (382 mg, 11.0 mmol) in dichloromethane (20 ml) and DIEA (to pH9). The mixture was stirred for 1 h at room temperature then (4-chloro-phenyl)-methyl amine (156 mg, 1.1 mmol) was added. The mixture was stirred for 2 days at room temperature then solvents were concentrated in vacuo. The residue was dissolved in EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (210 mg, 41%).

1. stirringThe mixture was stirred for 2 days at room temperature
2. concentrationsolvents were concentrated in vacuo
3. dissolutionThe residue was dissolved in EtOAC
4. washwashed with saturated NaHCO3
5. dry with materialbrine, dried
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

ORDレコード

ord-59342acd21c4412db3be6a29284765f2

出典データセット

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08202858B2