Diisopropylethylamine → HCID 71294340, compound

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Reaction Steps

In a 10 mL round-bottomed flask, the above prepared 2-(2,2,2-trifluoro-ethoxy)-3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-5,1′-dicarboxylic acid 1′-tert-butyl ester (100 mg, 247 mmol, Eq: 1.00) was combined with tetrahydrofuran (3 mL) and DMF (1 mL) to give a colorless solution. TBTU (119 mg, 371 μmol, Eq: 1.5) and N,N-diisopropylethylamine (160 mg, 216 μl, 1.24 mmol, Eq: 5) were added and the reaction mixture was stirred for 10 min at rt before 2-(1-aminopiperidin-4-yl)ethanol (61.1 mg, 297 μmol, Eq: 1.2, preparation see Example 38) was added and the reaction mixture kept overnight at rt. The reaction mixture was then quenched with sat NH4Cl sol. 10 mL and extracted with EtOAc (2×20 mL). The organic layers were washed with 1 M NaOH, then with H2O/NaCl sol., combined, dried over Na2SO4, and concentrated in vacuo. Purification by flash chromatography (silica gel, 20 g, 2% to 5% MeOH in DCM) delivered eventually 101 mg of the title compound as white foam; MS (EI) 531.6 (M+H)+.

Provenance & Evidence