Acetic Acid → HCID 178441315, compound

Participants

Reaction Steps

In a 20 mL vial, to a solution of Example 375C (52 mg, 0.118 mmol) in dichloromethane (2 mL) was added azetidine (20.22 mg, 0.354 mmol), followed by addition of acetic acid (7.09 mg, 0.118 mmol) and sodium triacetoxyborohydride (37.5 mg, 0.177 mmol) and the mixture was stirred for 2 hr. The reaction was quenched with saturated NaHCO3 and extracted with dichloromethane (3×5 mL). The organics were combined, dried, filtered, concentrated and the residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, gradient elution over 25 min with solvents A:B (100:0 to 10:90); solvent A=CH2Cl2; solvent B=7M NH3/MeOH (1):CH2Cl2 (9)) to afford the title compound in 79% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.34 (s, 9H) 1.61-1.76 (m, 1H) 1.79-1.91 (m, 2H) 1.91-2.06 (m, 3H) 3.18 (t, J=6.94 Hz, 4H) 3.60-3.71 (m, 1H) 3.74-3.85 (m, 1H) 4.06 (s, 2H) 4.23-4.36 (m, 3H) 7.32 (s, 1H) 7.74-7.78 (m, 2H) 8.21-8.25 (m, 1H); MS (DCI/NH3) m/z 482 (M+H)+. Anal. calcd C25H32F3N3O2S.0.3 C6H6: C, 62.02; H, 6.56; N, 8.10. Found: C, 61.94; H, 6.43; N, 8.38.

Provenance & Evidence