Water → HCID 10217923, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (0.18 mL) and N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 2, 0.250 g) were added to a solution of rac-5-(1-hydroxy-2-(methylamino)ethyl)thiophene-2-carbonitrile (Preparation 51, 0.188 g) in DMF (15 mL). The reaction mixture was heated to 90° C. for 2 h. The mixture was allowed to cool to room temperature and was poured into water (30 mL). The suspension was filtered and the resulting solid was purified by column chromatography (CH2Cl2/methanol; 98/2) followed by recrystallization from ethyl acetate/methanol to yield 0.111 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 190-195° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.63, 8.56, 7.80, 7.41-7.32, 7.14, 6.88, 6.06, 5.01-4.97, 4.55, 3.92, 3.76, 2.69-2.64, 2.34; 13C NMR (100 MHz, CDCl3) δ 173.7, 164.6, 154.3, 153.2, 150.0, 141.2, 137.4, 137.2, 132.8, 128.9, 128.7, 123.3, 116.9, 114.7, 114.3, 108.5, 106.9, 66.3, 63.9, 54.1, 42.6, 41.8, 37.8; MS (ESI+) m/z 511 (M+H)+.

Provenance & Evidence