Dabco → N-(2,4-dimethoxybenzyl)-2,4-difluoro-5-methyl-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 337781Notes

Reaction equation

HRID 337781 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[CH:25]=[C:24]([F:26])[C:23]([CH3:27])=[CH:22][C:21]=1[S:28](Cl)(=[O:30])=[O:29].N12CCN(CC1)CC2>C1COCC1>[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]=[C:23]([CH3:27])[C:24]([F:26])=[CH:25][C:20]=1[F:19])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 9237DabcoHCID 594365302,4-Difluoro-5-methylbenzenesulfonyl chlorideHCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

Product 1

HCID 89962229N-(2,4-dimethoxybenzyl)-2,4-difluoro-5-methyl-N-(pyrimidin-4-yl)benzenesulfonamideYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 14b by using the N-(2,4-dimethoxybenzyl)pyrimidin-4-amine (1.0 g, 4.08 mmol) prepared in Example 14a, 2,4-difluoro-5-methylbenzenesulfonyl chloride (WO 2010/079443; 1.85 g, 8.15 mmol), 1,4-diazabicyclo[2.2.2]octane (0.91 g, 8.15 mmol) and THF (20 mL), to yield the title compound (1.41 g, 79%) as a colorless amorphous solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-58baa7ffabab40fd9a0293ee49302979
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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