反应详情

To the solution of crude [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-thiazol-2-yl]-(4-fluoro-benzyl)-carbamic acid tert-butyl ester (628, 0.186 mmol theory) in dichloromethane (5 mL) at room temperature was added trifluoroacetic acid (1 mL) and the reaction was allowed to stir overnight. The solvent was removed in vacuo and the residue taken up in ethyl acetate and then washed with saturated aqueous potassium carbonate making sure basicity was reached. The layers were separated and the aqueous layer was back-extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated in vacuo to give the crude product which was purified by silica gel chromatography (0-10% methanol/ethyl acetate). The solvent was removed in vacuo and the material was triturated with dichloromethane to give the desired compound as an off-white solid (20 mg, 29% over 2 steps) consistent with compound structure by 1H-NMR and MS (ESI): [M+H+]+=372.9.

1. customThe solvent was removed in vacuo
2. washwashed with saturated aqueous potassium carbonate making sure basicity
3. customThe layers were separated
4. extractionthe aqueous layer was back-extracted with ethyl acetate
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. customevaporated in vacuo
7. customto give the crude product which
8. customwas purified by silica gel chromatography (0-10% methanol/ethyl acetate)
9. customThe solvent was removed in vacuo
10. customthe material was triturated with dichloromethane