Tris(hydroxymethyl)aminomethane → HCID 73504794, compound

Participants

Reaction Steps

To an 8 mL vial charged with ethanesulfonyl chloride (10.53 μL, 0.111 mmol) was added (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (Example 47, Step 1; 20 mg, 0.037 mmol) in DCM (1 mL) and pyridine (0.1 mL). The reaction mixture was stirred at room temperature for 2 h. Excess sulfonyl chloride was quenched by shaking with MP-Trisamine (91 mg, 0.186 mmol) for 3 h. The resin was filtered, the volatiles removed in vacuo, and the resulting residue dissolved in TFA (1 mL) and stirred at room temperature for 1 h. Triethylsilane (5.93 μL, 0.037 mmol) was added and the reaction mixture was stirred for an additional 5 min. The reaction mixture was concentrated in vacuo, the resulting crude residue dissolved in DMSO (1.5 mL), filtered, and purified by mass-triggered reverse phase HPLC to afford (R)—N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)ethanesulfonamide. MS ESI calc'd. For C17H20N6O3S [M+1]+ 389. found 389. 1H NMR (500 MHz, DMSO-d6) δ 12.74 (1H, s), 10.63 (1H, s), 9.20 (1H, s), 8.76 (1H, s), 7.70 (1H, s), 7.50 (1H, s), 7.31 (4H, d, J=4.4 Hz), 7.20-7.21 (1H, m), 4.84 (1H, t, J=7.2 Hz), 3.30 (2H, q, J=7.4 Hz), 1.38 (3H, d, J=7.0 Hz), 1.23 (3H, t, J=7.4 Hz).

Provenance & Evidence