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 868182Notes

Reaction equation

HRID 868182 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-cc0cf3ca6c534d609f44a30d7a06641b
Source dataset
uspto-grants-1988_10
Patent number
US04778513

Reaction notes

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