2H-pyran-3,5(4H,6H)-dione → 4-(2,1,3-benzoxadiazol-5-yl)-1-methyl-4,9-dihydro-1H-isoxazolo [3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

HRID 1862452Notes

Reaction equation

HRID 1862452 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[N:9]1[O:10][N:11]=[C:12]2[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:13]=12.[O:20]1[CH2:25][C:24](=O)[CH2:23][C:22](=[O:27])[CH2:21]1>C(O)C>[N:9]1[O:10][N:11]=[C:12]2[CH:17]=[C:16]([CH:18]3[C:23]4[C:22](=[O:27])[CH2:21][O:20][CH2:25][C:24]=4[NH:1][C:2]4[N:3]([CH3:8])[O:4][C:5](=[O:7])[C:6]3=4)[CH:15]=[CH:14][C:13]=12

Participants

5

Reactant 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 2776296Benzo(c)(1,2,5)oxadiazole-5-carbaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 99677714-(2,1,3-benzoxadiazol-5-yl)-1-methyl-4,9-dihydro-1H-isoxazolo [3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.11 g, 1 mmol), 2,1,3-benzoxadiazole-5-carboxaldehyde(0.15 g, 1 mmol), prepared as described in (Gasco, A. M., Ermondi, G. Eur. J. Med. Chem., (1996) 31, 3)and 2H-pyran-3,5(4H,6H)-dione (0.11 g, 1 mmol) were heated in 2 mL of ethanol for 2 days. The resulting mixture was allowed to cool to ambient temperature and filtered to provide the title compound as the filter cake (0.09 g). 1H NMR (300 MHz, DMSO-d6) δ 3.28 (s, 3H), 4.08 (s, 2H), 4.6 (q, 2H), 4.92 (s, 1H), 7.62 (dd, 1H), 7.76 (s, 1H), 8.0 (dd, 1H), 10.8 (s, 1H); MS (ESI) m/z 339 (M−H)−; Anal. Calcd for C16H12N4O5: C, 56.47; H, 3.52; N, 16.47. Found: C, 56.03;H, 3.97; N, 15.57.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-6035d75377354a2f83dc0d185841bf09
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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