1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 20261266, compound

HRID 464914Notes

Reaction equation

HRID 464914 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.N12CCCN=C1CCCCC2.[F:23][CH:24]([F:43])[O:25][C:26]1[CH:31]=[C:30]([CH3:32])[N:29]=[C:28]([N:33](C2C=CC=CC=2)[C:34](=O)[O-:35])[N:27]=1>O1CCOCC1>[Cl:1][C:2]1[C:7]([S:8]([NH:11][C:34]([NH:33][C:28]2[N:27]=[C:26]([O:25][CH:24]([F:43])[F:23])[CH:31]=[C:30]([CH3:32])[N:29]=2)=[O:35])(=[O:9])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 122344452-chloropyridine-3-sulfonamideHCID 86740387HCID 86740387, compound

Product 1

HCID 20261266HCID 20261266, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 0.652 g of 2-chloro-3-pyridinylsulfonamide and 0.55 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene in 10 ml of absolute dioxan is added, at 25° C., 1 g of N-(4-difluoromethoxy-6-methylpyrimidin-2-yl)phenylcarbamate. The reaction mixture is stirred for another 2 hours at the same temperature and then concentrated. The residue is taken up in ice/water and neutralised with 1.86 ml of 2N hydrochloric acid. The precipitate is isolated, washed with water and dreid, affording 1.2 g (90%) of N-(2-chloro-3-pyridinylsulfonyl)-N'-(4-difluoromethoxy-6-methylpyrimidin-2-yl)urea (compound 1.15) with a melting point of 161°-162° C.

Workup

  1. additionis added, at 25° C.
  2. concentrationconcentrated
  3. customThe precipitate is isolated
  4. washwashed with water and dreid

Sources & evidence

ORD record
ord-38af732e67a041199e279503d8ba113e
Source dataset
uspto-grants-1985_10
Patent number
US04549898

Reaction notes

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