1,2-Dichloroethane → HCID 57678519, compound

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Reaction Steps

4-(3-Amino-4-hydroxy-phenoxy)-pyridine-2-carboxylic acid (4-pyrrolidin-1-yl-butyl)-amide (Example 253, Step E, 165 mg, 0.4 mmol, 1.0 eq.) was dissolved in CH3CN/DMF (2/1, v/v, 15 ml) and 1-chloro-4-isothiocyanato-benzene (as described in preparation III, 75 mg, 0.4 mmol, 1.0 eq.) in as a CH3CN solution was added dropwise. The reaction was stirred at RT for 16 h. EDC (85 mg, 0.4 mmol, 1.0 eq.) was added and the reaction was heated to 80° C. for 2 h. The mixture was concentrated and the crude product was purified by column chromatography (0-10% MeOH/CH2Cl2/1% NH4OH) to yield 4-[2-(4-chloro-phenylamino)-benzoxazol-5-yloxy]-pyridine-2-carboxylic acid (4-pyrrolidin-1-yl-butyl)-amide. MS m/z=506.01 (M+H)+Calc'd for C27H28ClN5O3: 505.19.

Provenance & Evidence