Methanol → Methyl [1,2,4]triazolo[1,5-A]pyridine-7-carboxylate

温度

130 °C

To a solution of methyl 2-aminoisonicotinate (28.8 g, 191 mmol) in DMF (97.5 mL) was added DMF-DMA (70.6 mL, 496 mmol) and the mixture heated to 130° C. for 12 hours. The mixture was then concentrated to give a residue. To the residue was added methanol (381 mL), followed by NH2OHSO4 (31.9 g, 248 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated to give methyl[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate in 18% yield, 6 g. To a solution of methyl[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (3 g, 16 mmol) in methanol was added 1M aq. LiOH (70 mL) and the resulting mixture stirred for 10 hours at room temperature. The pH was adjusted to 5-6 using aq. HCl and the whole mixture extracted with EtOAc (30 mL×3). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound as white solid in 38% yield, 1.05 g 1H NMR (400 MHz, DMSO-d6): δ13.5-14.0 (s, 1H), 9.04-9.06 (m, 1H), 8.66 (m, 1H), 8.32 (m, 1H), 67.56-7.58 (m, 1H).

1. concentrationThe mixture was then concentrated
2. customto give a residue
3. concentrationThe reaction mixture was concentrated

ORDレコード

ord-60d7a884e85f4a6abda66b84d849d137

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08846698B2