2-PYRIDINECARBOXAMIDE, 5-HYDROXY- synthesis

Yield: 7%

Reaction Conditions:

with ammonium chloride;N-ethyl-N,N-diisopropylamine;HATU in N,N-dimethyl-formamide at 20;

Steps:

vii (vii) 5-Hydroxypicolinamide (111 )
A suspension of 5-hydroxypicolinic acid (1 g, 7.2 mmol), NhUCI (3.8 g, 72 mmol), HATU (3.3 g, 8.64 mmol) and DIPEA (2.8 g, 21 .6 mmol) in DMF (20 ml.) was stirred at room temperature overnight. Water (100 ml.) was added and the mixture was extracted with EtOAc (50 ml. x 3). The combined organic extracts were washed with brine (100 ml_), dried over anhydrous Na2S0₄, filtered and concentrated under reduced pressure to give the title product (65 mg, 7%) as a white solid. LCMS-C: rt 0.98 min, m/z 139.1 [M+H]⁺.

References:

CTXT PTY LIMITED;MORROW, Benjamin, Joseph;CAMERINO, Michelle, Ang;WALKER, Scott, Raymond;STEVENSON, Graeme, Irvine;STUPPLE, Paul, Anthony WO2019/219820, 2019, A1 Location in patent:Page/Page column 105