Potassium Phosphate, Tribasic → HCID 86617878, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S)-1-[(1S,2S)-2-methylcyclopropyl]ethanaminium chloride (intermediate P, 0.039 g, 0.29 mmol) and tert-butyl (1R)-1-(2-{2-chloro-6-[methyl(methylsulfonyl)amino]pyridin-4-yl}-1,3-oxazol-5-yl)-1-methyl-2-phenylethylcarbamate (intermediate k, 0.050 g, 0.10 mmol) in 1 mL DMF was added K3PO4 (0.122 g, 0.58 mmol) and Pd(PtBu3)2 (0.007 g, 0.01 mmol). After 16 h at ambient temperature, the sealed reaction was heated at 110° C. for 8.5 h and then filtered over a pad of celite. The celite was washed with EtOAc (60 mL). The filtrate was concentrated in vacuo and the resulting residue taken up in DMF and purified by reverse phase LC. The resulting material was diluted with EtOAc (40 mL) and washed with saturated sodium bicarbonate solution (20 mL). The aqueous layer was back extracted with EtOAc (20 mL). The combined organics were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo to give 0.028 g (50%) of tert-butyl (1R)-1-methyl-1-(2-{2-({(1S)-1-[(1S,2S)-2-methylcyclopropyl]ethyl}amino)-6-[methyl(methylsulfonyl)amino]pyridin-4-yl}-1,3-oxazol-5-yl)-2-phenylethylcarbamate as a yellow residue. (CDCl3, 400 MHz) 7.28 (m 3H); 7.06 (d, J=0.91 Hz, 1H); 7.03 (m, 2H); 6.93 (s, 1H); 6.76 (s, 1H); 3.50 (m, 1H); 3.36 (m, 4H); 14 (m, 4H); 1.60 (s, 3H); 1.42 (s, 9H); LC/MS [M+H]+=584.

Provenance & Evidence