Dabco → N-(2,4-dimethoxybenzyl)-4-fluoro-N-(pyrimidin-4-yl)-3-(trifluoromethyl)benzenesulfonamide

HRID 337741

Reaction equation

HRID 337741 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]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][C:21]=1[C:30]([F:33])([F:32])[F:31].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:26]([C:23]1[CH:24]=[CH:25][C:20]([F:19])=[C:21]([C:30]([F:33])([F:31])[F:32])[CH:22]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 9237DabcoHCID 27375494-Fluoro-3-(trifluoromethyl)benzenesulfonyl ChlorideHCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

Product 1

HCID 89963734N-(2,4-dimethoxybenzyl)-4-fluoro-N-(pyrimidin-4-yl)-3-(trifluoromethyl)benzenesulfonamideYield 33%

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)pyrimidin-4-amine (150 mg, 0.611 mmol) prepared in Example 14a, 4-fluoro-3-(trifluoromethyl)benzenesulfonyl chloride (321 mg, 1.22 mmol), 1,4-diazabicyclo[2.2.2]octane (137 mg, 1.22 mmol) and acetonitrile (5.0 mL), to yield the title compound (94.7 mg, 33%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-79f5abb12eef418c85d1d1507b1ba608
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Linked notes

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