Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86665065, compound

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Reaction Steps

To a solution of 1-(2-chloroallyl)cyclopentanecarboxylic acid (51 mg, 0.27 mmol) in DMF (1 mL) and CH2Cl2 (2 mL) was added (S)-2-amino-3-(biphenyl-4-yl)-N,N-dimethylpropanamide TFA salt (109 mg, 0.41 mmol) and TEA (0.19 mL, 1.35 mmol). To the mixture at room temperature was added HATU (154 mg, 0.41 mmol) and stirred at room temperature for 47 hours. The mixture was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by TLC preparation plates using 70% EtOAc/heptane to give (S)—N-(3-(biphenyl-4-yl)-1-(dimethylamino)-1-oxopropan-2-yl)-1-(2-chloroallyl)cyclopentanecarboxamide (83 mg). HPLC retention time=1.76 minutes (condition B); MS (m+1)=439.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38-1.66 (m, 5H), 1.89-2.05 (m, 3H), 2.64 (d, J=15.3 Hz, 1H), 2.70 (d, J=15.3 Hz, 1H), 2.85 (s, 3H), 2.95 (s, 3H), 2.95 (dd, J=13.6, 6.1 Hz, 1H), 3.05 (dd, J=13.6, 6.1 Hz, 1H), 5.05 (s, 1H), 5.10 (s, 1H), 5.08-5.13 (m, 1H), 6.70 (d, J=8.1 Hz, 1H), 7.29 (d, J=8.1 Hz, 2H), 7.32-7.38 (m, 1H), 7.44 (t, J=7.7 Hz, 2H), 7.54 (d, J=8.1 Hz, 2H), 7.58-7.65 (m, 2H).

Provenance & Evidence