3-Amino-5-methylisoxazole → 1-{[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}ethanone

HRID 2397596Notes

Reaction equation

HRID 2397596 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=O)(=O)[N:4](C)[C:3]=1[C:15](=[O:23])[NH:16][C:17]1[CH:21]=[C:20]([CH3:22])[O:19][N:18]=1.NC1C=C(C)ON=1.CC1ON=C(NC(=O)CN2C(=O)C3C=CC=CC=3S2(=O)=O)C=1>>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][NH:4][C:3]=1[C:15]1[O:23][N:18]=[C:17]([CH2:21][C:20](=[O:19])[CH3:22])[N:16]=1

Participants

4

Reactant 3

HCID 661723-Amino-5-methylisoxazoleHCID 24255921,2-Benzisothiazole-2(3H)-acetamide, N-(5-methyl-3-isoxazolyl)-3-oxo-, 1,1-dioxideHCID 54677972Isoxicam2×

Product 1

HCID 1357485761-{[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}ethanone

Procedure

A novel process for preparing 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (I), starting with 3-amino-5-methylisoxazole (II) is disclosed. Compound I exhibits anti-inflammatory properties and is useful for treating inflammation. In the process of the invention an intermediate obtained, 2,3-dihydro-N-(5-methyl-3-isoxazolyl)-3-oxo-1,2-benzisothiazole-2-actamide 1,1-dioxide (IV) undergoes rearrangement to provide 1-{[5-(4-hydroxy-2H-1,2-benzothiazin-3-yl)-1,2,4-oxadiazol-3-yl]methyl}ethanone, S,S-dioxide (V), which is methylated, according to conventional procedures. The methylated intermediate VI, upon further treatment, undergoes a second rearrangement to obtain the desired anti-inflammatory compound I.

Workup

  1. additionfor treating inflammation
  2. customIn the process of the invention an intermediate obtained

Sources & evidence

ORD record
ord-3fc3b8d8200641638062677b92c0948f
Source dataset
uspto-grants-1977_05
Patent number
US04022796

Reaction notes

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