Diisopropylethylamine → 5-Fluoro-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

To a solution of 5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid (400 mg, 2.27 mmol), 2-amino-5-fluoro-indan-2-carboxylic acid ethyl ester (610 mg, 2.72 mmol), HATU (1.30 g, 3.41 mmol) in anhydrous DMF (15 mL) is added DIPEA (563 μL, 3.41 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (70 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 5%-40% EtOAc in heptane) to give a pure product (86) as white solid (345 mg, 40%).

1. customAfter the removal of DMF in vacuo
2. dissolutionthe residue is dissolved in EtOAc (70 mL)
3. washwashed with water (1×10 mL) and brine (2×10 mL)
4. dry with materialThe organic layer is dried over anhydrous Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue is purified by flash column chromatography (115 g silica gel, gradient elution: 5%-40% EtOAc in heptane)

ORDレコード

ord-0279c80a778f479bb9806aeac27986f2

出典データセット

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08569535B2