Dabco → N-(2,4-Dimethoxybenzyl)-2,3,4-trifluoro-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 337758Notes

Reaction equation

HRID 337758 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][N:8]=1.[F:19][C:20]1[C:25]([F:26])=[C:24]([F:27])[CH:23]=[CH:22][C:21]=1[S:28](Cl)(=[O:30])=[O:29].N12CCN(CC1)CC2>C(#N)C>[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][N:8]=1)[S:28]([C:21]1[CH:22]=[CH:23][C:24]([F:27])=[C:25]([F:26])[C:20]=1[F:19])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 9237DabcoHCID 27769772,3,4-Trifluorobenzenesulfonyl chlorideHCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

Product 1

HCID 89962337N-(2,4-Dimethoxybenzyl)-2,3,4-trifluoro-N-(pyrimidin-4-yl)benzenesulfonamideYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 14b by using the N-(2,4-dimethoxybenzyl)pyrimidine-4-amine (400 mg, 1.63 mmol) prepared in Example 14a, 2,3,4-trifluorobenzenesulfonyl chloride (752 mg, 3.26 mmol), 1,4-diazabicyclo[2.2.2]octane (366 mg, 3.26 mmol) and acetonitrile (8.0 mL), to yield the title compound (221 mg, 31%) as a colorless amorphous solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-d75f4f88f7f8429a9071b5897136daae
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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