Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 58125481, compound

To a stirred solution of 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-3-carboxylic acid (8.14 g, 48.4 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.21 g, 53.3 mmol), 1-hydroxybenzotriazole hydrate (8.16 g, 53.3 mmol), 4-dimethylaminopyridine (300 mg, 2 mmol), and DIPEA (16.5 mL, 97 mmol) in anhydrous acetonitrile (200 mL) was added a solution of N,O-dimethylhydroxylamine hydrochloride (9.44 g, 97 mmol) and DIPEA (16.5 mL, 97 mmol) in anhydrous acetonitrile (100 mL). The mixture was stirred for 3 days at room temperature, then poured into saturated NaHCO3 solution (200 mL) and extracted with EtOAc (3×1000 mL). The combined organic layers were washed with brine (200 mL), dried (Na2SO4), filtered and concentrated. Flash chromatography (0 to 5% MeOH in DCM) afforded the amide as a solid (9.02 g, 88%). 1H NMR (400 MHz, DMSO-d6) δ7.62 (s, 1H), 4.35 (t, 2H, J=5.24 Hz), 4.08 (t, 2H, J=6.20 Hz), 3.63 (s, 3H), 3.12 (s, 3H), 2.20-2.15 (m, 2H).

1. extractionextracted with EtOAc (3×1000 mL)
2. washThe combined organic layers were washed with brine (200 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated

ORD record

ord-ef4c4f76913e43a2aabb440b127fecf8

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163901B2