HCID 131734501, compound → HCID 73505858, compound

Participants

Reaction Steps

To the solution of (S)-methyl 2-(3-(3-((tert-butoxycarbonyl)(ethyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)ureido)-2-phenylacetate (0.078 g, 0.109 mmol) in anhydrous CH2Cl2 (1 mL) was added TFA (imp followed by Et3SiH (2 drops). The resultant mixture was stirred at ambient temperature. After 2 h of stirring, solvent was removed under reduced pressure, the residue (TFA salt) thus obtained was triturated in diethyl ether to afford the compound which was taken as such for next step. At 0° C., to the solution of [3-(3-Ethylamino-1H-pyrazolo[4,3-c]pyridin-6-yl)-ureido]-phenyl-acetic acid methyl ester TFA salt (0.06 g, 0.163 mmol) in anhydrous THF was added methyl magnesium bromide (1 M solution in toluene, 1.63 mL, 1.63 mmol) and resultant mixture was allowed to warm and stirred at ambient temperature. After 10 h, the reaction was quenched with saturated aqueous NH4Cl solution (5 mL), and the organic contents were extracted with CH2Cl2 (3×10 mL). The volatiles were removed under reduced pressure and the residue thus obtained was further purified by prep HPLC to afford the title compound. 1H NMR (ppm, 400 MHz, CD3OD): δ 8.69 (s, 1H), 7.44-7.39 (m, 2H), 7.33-7.29 (m, 2H), 7.26-7.23 (m, 1H), 6.99 (s, 1H), 4.78 (s, 1H), 3.36 (q, J=7.2 Hz, 2H), 1.31 (t, J=7.1 Hz, 3H), 1.30 (s, 3H), 1.16 (s, 3H). MS ESI calc'd. for C19H24N6O2 [M+H]+ 369. Found 369.

Provenance & Evidence