Trifluoroacetic acid → HCID 67252221, compound

Participants

Reaction Steps

A suspension of {6-[2-(2,5-dimethoxy-benzylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.32 g, 0.69 mmol) in CH2Cl2 (10 mL) was treated with trifluoroacetic acid (1 mL, 12.98 mmol) and refluxed for 18 hours. A second portion of trifluoroacetic acid was added (1 mL, 12.98 mmol) and the solution was refluxed for another 18 hours. The mixture was concentrated and purified by preparative HPLC (CH3CN/0.1% formic acid in water) to give [6-(2-amino-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid formic acid salt as a white solid (0.10 g, 46%) after lyophilization. 1H NMR (400 MHz, DMSO-d δ9.26 (br s, 1H), 8.14 (d, J=6.24 Hz, 1H), 8.11 (s, 1H), 7.24 (d, J=2.34 Hz, 1H), 7.17 (br s, 2H), 7.08 (d, J=2.34 Hz, 1H), 6.26 (d, J=5.86 Hz, 1H), 5.51 (dd, J=9.76, 2.73 Hz, 1H), 3.08 (dd, J=15.61, 2.73 Hz, 1H), 2.29 (d, 3H), 2.10 (dd, J=15.76, 9.76 Hz, 1H). MS (ESI) m/z: 316 [M+1].

Provenance & Evidence