Dabco → 4-(2-Oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-n-(pyrimidin-4-yl)benzenesulfonamide

HRID 1715907Notes

Reaction equation

HRID 1715907 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.C1N2CCN(CC2)C1.[O:16]=[C:17]1[CH2:22][N:21]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:20][CH2:19][N:18]1[C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C(#N)C>[O:16]=[C:17]1[CH2:22][N:21]([C:23](=[O:28])[C:24]([F:26])([F:25])[F:27])[CH2:20][CH2:19][N:18]1[C:29]1[CH:30]=[CH:31][C:32]([S:35]([NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][N:3]=2)(=[O:37])=[O:36])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 689584-AminopyrimidineHCID 59465974HCID 59465974, compound

Product 1

HCID 594662384-(2-Oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-n-(pyrimidin-4-yl)benzenesulfonamideYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized according to general procedure 12, method B. The reaction was set up with 4-aminopyrimidine (0.26 g, 2.16 mmol), anhydrous acetonitrile (10 mL), DABCO (0.24 gm, 2.16 mmol) and 4-(2-oxo-4-(2,2,2-trifluoroacetyl)piperazin-1-yl)benzene-1-sulfonyl chloride (0.80 g, 2.16 mmol). The dark oil was purified via silica gel chromatography using 5% MeOH in CH2Cl2 followed by a second purification on silica gel using 80% methanol in dichloromethane to obtain the desired sulfonamide as a white solid (0.43 g, 0.93 mmol, 47% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=439.3; tR=2.3 min

Workup

  1. customSynthesized
  2. customThe dark oil was purified via silica gel chromatography
  3. customfollowed by a second purification on silica gel using 80% methanol in dichloromethane

Sources & evidence

ORD record
ord-1bf85b9ed63a4a278d74727481e5da22
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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