1,8-Diazabicyclo(5.4.0)undec-7-ene → 4,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl-N[(4-methyl-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 34876Notes

Reaction equation

HRID 34876 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[O:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([NH2:17])(=[O:16])=[O:15])=[N:3]1.C1([O:24][C:25](=O)[NH:26][C:27]2[N:32]=[C:31]([CH3:33])[N:30]=[C:29]([O:34][CH3:35])[N:28]=2)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>O1CCOCC1>[CH3:1][N:2]1[C:6](=[O:7])[O:5][C:4]([C:8]2[C:9]([S:14]([NH:17][C:25]([NH:26][C:27]3[N:32]=[C:31]([CH3:33])[N:30]=[C:29]([O:34][CH3:35])[N:28]=3)=[O:24])(=[O:16])=[O:15])=[CH:10][CH2:11][CH2:12][CH:13]=2)=[N:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11448329Carbamic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl)-, phenyl esterHCID 139588572-(4,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)benzenesulfonamide

Product 1

HCID 1317153324,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl-N[(4-methyl-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

By the procedure of Example 5, 0.4 g of the product of Example 4 was reacted with 0.41 g of phenyl(4-methyl-6-methoxy-1,3,5-triazin-2-yl)carbamate and 0.24 g of "DBU" in 10 ml of p-dioxane. The isolated crude solid was purified by slurry-washing with 10 ml of warm acetonitrile to yield 0.3 g of the subject compound; m.p. 198°-200° C.

Workup

  1. customThe isolated crude solid
  2. customwas purified
  3. washby slurry-washing with 10 ml of warm acetonitrile

Sources & evidence

ORD record
ord-b574c385f93248b481f743ff12afec51
Source dataset
uspto-grants-1988_08
Patent number
US04764205

Reaction notes

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