Diisopropylethylamine → 4-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

To a mixture of 0.5 g (2.79 mmol) of 4-amino-tetrahydro-pyran-3-carboxylic acid methyl ester [WO 01/70673, Example 207] and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (1.0 g, 2.94 mmol) in N,N-dimethylformamide (10 mL) was added N,N-diisopropylethylamine (1.02 mL, 5.88 mmol) at 0° C. The solution was allowed to warm to 25° C. over 19 h. The DMF was removed in vacuo and the resulting solid was partitioned between ethyl acetate (100 mL) and water (30 mL). The aqueous layer was washed with ethyl acetate (2×50 mL). ). The organic layer was dried over MgSO4, filtered and concentrated to obtain a crude oil (1.48 g). The crude product was purified by Biotage Flash 40M chromatography, eluting with 1:4 ethyl acetate-hexanes, to afford 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-pyran-3-carboxylic acid methyl ester as a white solid (1.08 g, 78%). MS: 471 (M+H)+

Provenance & Evidence