Carbodiimide → HCID 178429248, compound

Participants

Reaction Steps

The product from Example 2, Step 2 (170 mg, 0.68 mmol, 1.0 equiv) was combined with 3-chloro-1H-indazol-5-amine (172 mg, 1.02 mmol, 1.5 equiv) and PS-carbodiimide resin (0.994 mmol/g loading, 1.085 g, 1.02 mmol, 1.5 equiv) in 10 mL of DMF and reacted overnight at room temperature. The reaction mixture was filtered and washed alternately with MeOH and CH2Cl2 (twice), then with diethyl ether. The filtrate was concentrated en vacuo and redissolved in ethyl acetate. The solution was washed with 0.5 N HCl, 0.5 N NaOH, and satd. NaCl. The organic layer was concentrated en vacuo. Purification by flash chromatography (0-50% EtOAc in CH2Cl2) followed by trituration with CH2Cl2 provided 45 mg (16.5%) of the title compound as light pink crystals. MS (ES+) m/e 399 [M+H]+.

Provenance & Evidence