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

HRID 337745

Reaction equation

HRID 337745 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.[Cl:19][C:20]1[CH:21]=[C:22]([S:27](Cl)(=[O:29])=[O:28])[CH:23]=[CH:24][C:25]=1[F:26].N12CCN(CC1)CC2>C(#N)C>[Cl:19][C:20]1[CH:21]=[C:22]([S:27]([N:6]([CH2:5][C:4]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:3]=2[O:2][CH3:1])[C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]=2)(=[O:28])=[O:29])[CH:23]=[CH:24][C:25]=1[F:26]

Participants

5

Reactant 3

HCID 9237DabcoHCID 1452223-Chloro-4-fluorobenzenesulphonyl chlorideHCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

Product 1

HCID 899628723-Chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(pyrimidin-4-yl)benzenesulfonamideYield 47.5%

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, 3-chloro-4-fluorobenzenesulfonyl chloride (280 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 (127 mg, 47%) as a colorless amorphous solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-579ecf08e98b4842b3ea18363d914744
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Linked notes

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