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

HRID 236240Notes

Reaction equation

HRID 236240 reaction equation
[CH:1]1([O:6][C:7]2[C:12]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.[CH3:28][O:29][C:30]1[N:35]=[C:34]([CH3:36])[N:33]=[C:32]([N:37](C2C=CC=CC=2)[C:38](=O)[O-:39])[N:31]=1>O1CCOCC1>[CH:1]1([O:6][C:7]2[C:12]([S:13]([NH:16][C:38]([NH:37][C:32]3[N:31]=[C:30]([O:29][CH3:28])[N:35]=[C:34]([CH3:36])[N:33]=3)=[O:39])(=[O:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 198537212-Cyclopentyloxypyridin-3-ylsulfonamideHCID 199952694-Methoxy-6-methyl-1,3,5-triazin-2-ylphenylcarbamate

Product 1

HCID 19853724N-(2-cyclopentyloxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaYield 95.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4.84 g of 2-cyclopentyloxypyridin-3-ylsulfonamide and 3.13 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene in 50 ml of absolute dioxan are added 5.46 g of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenylcarbamate at 20° to 25° C. The mixture is stirred for 1/2 hour, the precipitate is isolated and the filtrate is concentrated by evaporation. The residue is triturated with 10 ml of 2N hydrochloric acid and the crystals so obtained are isolated, washed with ether and water and dried, affording 7.79 g of N-(2-cyclopentyloxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea with a melting point of 170°-172° C.

Workup

  1. customthe precipitate is isolated
  2. concentrationthe filtrate is concentrated by evaporation
  3. customThe residue is triturated with 10 ml of 2N hydrochloric acid
  4. customthe crystals so obtained
  5. customare isolated
  6. washwashed with ether and water
  7. customdried

Sources & evidence

ORD record
ord-4d16b0341cf54b119d621d92a6791da3
Source dataset
uspto-grants-1987_02
Patent number
US04643760

Reaction notes

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