Formamide → (1S)-1-(1-{[2-cyano-4-(1,3-thiazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

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Reaction Steps

To a solution of P4S10 (34 mg, 0.08 mmol) in dioxane (1 mL) at 0° C. was added formamide (57 mg, 1.26 mmol). The reaction mixture was warmed to room temperature for 1 h. A solution of 1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (see Example 52, Step 2) (160 mg, 0.25 mmol) in dioxane (1 mL) was then added and the mixture stirred at room temperature overnight. The reaction mixture was diluted in ethyl acetate, washed with water, brine and dried over MgSO4. The crude compound was purified on silica gel (eluting solvent: 5% acetone in dichloromethane) to give the desired product. 1H NMR (acetone-d6): δ 9.35 (s, 1H), 8.80 (d, 1H), 8.55 (s, 1H), 8.40 (m, 3H), 8.30 (d, 2H), 8.22 (s, 1H), 8.05 (s, 1H), 7.75 (d, 1H), 6.05 (s, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 1.15 (t, 3H).

Provenance & Evidence