6,7-Dimethoxy-2H-3,1-benzoxazine-2,4(1H)-dione → 7,8-dimethoxy-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione

HRID 1297094Notes

Reaction equation

HRID 1297094 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:16][CH3:17])=[CH:5][C:6]2[N:11](C)[C:10](=[O:13])[O:9][C:8](=O)[C:7]=2[CH:15]=1.COC1C(OC)=CC2[NH:28][C:27](=O)OC(=O)C=2C=1>>[CH3:1][O:2][C:3]1[C:4]([O:16][CH3:17])=[CH:5][C:6]2[NH:11][C:10](=[O:13])[CH2:27][NH:28][C:8](=[O:9])[C:7]=2[CH:15]=1

Participants

3

Reactant 2

HCID 27584236,7-Dimethoxy-2H-3,1-benzoxazine-2,4(1H)-dioneHCID 122232926,7-Dimethoxy-1-methyl-1H-benzo(d)(1,3)oxazine-2,4-dione

Product 1

HCID 694609827,8-dimethoxy-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dioneYield 54%

Procedure

By replacing 6,7-dimethoxy-1-methyl-11,2-dihydro-4H-3,1-benzoxazine-2,4-dione (XVI) in example XVIIaa by 6,7-dimethoxy-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione (XV) and proceeding in the same manner, the abovenamed product is obtained. Yield: 54%. 1H-NMR (DMSO, 300 MHz): d 3.55 (d, J=5.3, 2H, CH2), 3.77 (s, 6H, 2×OCH3), 6.16 (s, 1H Ar), 6.67 (s, 1H Ar), 8.34 (t, J=5.3, 1H, NH), 10.07 (s, 1H, NH).

Workup

  1. customthe abovenamed product is obtained

Sources & evidence

ORD record
ord-6e5486a09fd44b43a3c4e49954c85920
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

Loading…