Diisopropylethylamine → 5-Cyano-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 (306 mg, 1.74 mmol), 2-amino-5-cyano-indan-2-carboxylic acid ethyl ester (601 mg, 2.61 mmol), HATU (992 mg, 2.61 mmol) in anhydrous DMF (15 mL) is added DIPEA (431 μL, 2.61 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 (120 g silica gel, gradient elution: 5%-80% EtOAc in heptane) to give a pure product (106) as white solid (473 mg, 70%).

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 (120 g silica gel, gradient elution: 5%-80% EtOAc in heptane)

ORD-Eintrag

ord-8f83365e62074dd38e828da2911ced35

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08569535B2