Potassium Carbonate → 3-amino-N-methoxypyridine-2-carboxamide

HRID 2279835Notes

Reaction equation

Cl.[O:2]([NH2:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[NH:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[N:20][C:15]=2[C:14](=O)[O:13]C1=O>O>[NH2:11][C:16]1[C:15]([C:14]([NH:4][O:2][CH3:3])=[O:13])=[N:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of Methoxylamine hydrochloride (1.02 g, 12.2 mmol) in H2O (5.0 mL) was treated with Potassium carbonate (0.421 g, 3.05 mmol) followed by 1H-pyrido[3,2-d][1,3]oxazine-2,4-dione (J. Med. Chem., 1996, 39, 4962-4703, 1.0 g, 6.1 mmol). This mixture was allowed to stir at 50° C. for ˜1 hour forming a suspension. The ppt was collected via filtration and the filtrate was stored in the freezer O/N allowing an additional 35 mg to be collected. The solids were combined to afford 257 mg of the title compound (22%). 1H NMR (400 MHz, DMSO-d6) d 11.62 (s, 1H), 7.75 (dd, J=1.4, 4.2 Hz, 1H), 7.23 (dd, J=4.2, 8.5 Hz, 1H), 7.15 (dd, J=1.4, 8.5 Hz, 1H), 6.74 (br. s., 2H), 3.65 (s, 3H).

Workup

customforming a suspension
filtrationThe ppt was collected via filtration
customto be collected

Sources & evidence

ORD record: ord-140a9b3397394ea98077a46f957bd410
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133224B2

Reaction notes

Loading…