HCID 67042921, compound → HCID 51036678, compound

HRID 2039535Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3O[C:13](=O)[C:14]4[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][C:15]=4[N:16]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)(O)O.[NH2:30][NH:31][C:32]([NH2:34])=[NH:33]>N1C=CC=CC=1>[NH2:34][C:32]1[N:33]=[C:13]2[N:30]([C:11]([CH2:10][C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)=[N:16][C:15]3[CH:17]=[C:18]([S:21]([NH2:24])(=[O:23])=[O:22])[CH:19]=[CH:20][C:14]=32)[N:31]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 2-(2-benzo[1,3]dioxol-5-yl-acetylamino)-4-sulfamoyl-benzoic acid (0.10 g, 0.26 mmol), acetic acid (1.5 mL) and acetic anhydride (0.10 mL, 1.06 mmol) was stirred at reflux for 1 h. The reaction was diluted with ethyl acetate and washed with NaHCO3 satured solution, then with water and brine. The organic phase was dried over Na2SO4, filtered and evaporated to give the 2-benzo[1,3]dioxol-5-ylmethyl-4-oxo-4H-benzo[d][1,3]oxazine-7-sulfonic acid amide intermediate (0.032 g) as yellow oil. To a solution of 2-benzo[1,3]dioxol-5-ylmethyl-4-oxo-4H-benzo[d][1,3]oxazine-7-sulfonic acid amide (0.032 g, 0.09 mmol) in dry pyridine (1 mL) was added aminoguanidine hydrogencarbonate (0.013 g, 0.098 mmol) and the mixture was heated under microwave condition at 180° C. for 1.5 h. The solvent was then evaporated and the crude was taken up in methanol to give the title compound (0.013 g, 12% yield).

Workup

customThe solvent was then evaporated

Sources & evidence

ORD record: ord-ff622175ad7d4e6099c320bc155fff9d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580783B2

Reaction notes

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