2-(benzo[1,3]dioxol-5-yl)-3-hydroxy-6-amino-4H-1-benzopyran-4-one → N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-N'-cyclohexylsulfamide

HRID 2301348Notes

Reaction equation

HRID 2301348 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([C:12]1[CH:20]=[CH:19][C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=1)=[C:6]([OH:21])[C:5]2=[O:22].[CH:23]1([NH:29][S:30](Cl)(=[O:32])=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>N1C=CC=CC=1.O>[O:16]1[C:15]2[CH:19]=[CH:20][C:12]([C:7]3[O:8][C:9]4[C:4]([C:5](=[O:22])[C:6]=3[OH:21])=[CH:3][C:2]([NH:1][S:30]([NH:29][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)(=[O:32])=[O:31])=[CH:11][CH:10]=4)=[CH:13][C:14]=2[O:18][CH2:17]1

Participants

5

Reactant 2

HCID 99262072-(benzo[1,3]dioxol-5-yl)-3-hydroxy-6-amino-4H-1-benzopyran-4-oneHCID 12914615Cyclohexylsulfamyl chloride

Product 1

HCID 9804188N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-N'-cyclohexylsulfamideYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

30 mg (101 pmol) of 6-amino-2-(benzo[1,3]dioxol-5-yl)-3-hydroxy-4H-chromen-4-one obtained in Example 24 was dissolved in 3 ml of pyridine, and the mixture was reacted with excess amount of cyclohexylamino sulfonylchloride at room temperature for 15 hours. After the reaction was completed, the resulting product was diluted with 10 ml of water. The produced solid was filtered, washed with water and ethylether, and then dried to give 6 mg of the title compound in a yield of 13%.

Workup

  1. filtrationThe produced solid was filtered
  2. washwashed with water and ethylether
  3. customdried

Sources & evidence

ORD record
ord-2d5fd1ec7dae4b7ba929df081774b53d
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

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