1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(2-cyclopropylmethoxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea

HRID 236242Notes

Reaction equation

HRID 236242 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.[CH3:27][O:28][C:29]1[N:34]=[C:33]([CH3:35])[N:32]=[C:31]([N:36](C2C=CC=CC=2)[C:37](=O)[O-:38])[N:30]=1>O1CCOCC1>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([S:12]([NH:15][C:37]([NH:36][C:31]3[N:30]=[C:29]([O:28][CH3:27])[N:34]=[C:33]([CH3:35])[N:32]=3)=[O:38])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 198537232-Cyclopropylmethoxypyridin-3-ylsulfonamideHCID 199952694-Methoxy-6-methyl-1,3,5-triazin-2-ylphenylcarbamate

Product 1

HCID 19853722N-(2-cyclopropylmethoxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaYield 87.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.56 g of 2-cyclopropylmethoxypyridin-3-ylsulfonamide and 3.13 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene are suspended in 50 ml of dioxan and to this suspension are added 5.46 g of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenylcarbamate. The mixture is stirred for 20 minutes and concentrated by evaporation. The residue is triturated with 10 ml of 2N hydrochloric acid and the precipitated solid is isolated and washed with water and ether, affording 6.90 g of N-(2-cyclopropylmethoxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea with a melting point of 165°-167° C.

Workup

  1. concentrationconcentrated by evaporation
  2. customThe residue is triturated with 10 ml of 2N hydrochloric acid
  3. customthe precipitated solid is isolated
  4. washwashed with water and ether

Sources & evidence

ORD record
ord-0dbf9425ab0248d2981ecaaff4375b0d
Source dataset
uspto-grants-1987_02
Patent number
US04643760

Reaction notes

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