Pyridine → HCID 178486174, compound

HRID 276781Notes

Reaction equation

HRID 276781 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[C:17]([C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[N:24][CH:25]=3)[NH:18][CH:19]=2)=[CH:11][CH:10]=1.N1C=CC=CC=1>C1COCC1>[CH3:1][N:2]([CH3:7])[S:3]([N:29]1[CH2:28][CH2:27][N:26]([C:23]2[CH:22]=[CH:21][C:20]([C:17]3[NH:18][CH:19]=[C:15]([C:12]4[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=4)[N:16]=3)=[CH:25][N:24]=2)[CH2:31][CH2:30]1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 83372Dimethylsulphamoyl chlorideHCID 178505527HCID 178505527, compound

Product 1

HCID 178486174HCID 178486174, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dimethylsulfamoyl chloride (0.09 g) was added to a solution of 1-{5-[4-(4-Fluoro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine (0.2 g) and pyridine (0.05 g) in THF. The reaction mixture was held at room temperature overnight and then concentrated in vacuo. The residue was diluted with 1 N NaOH and the resultant mixture extracted with dichloromethane. The organics were extracted with 6N HCl, and the acidic extracts basified with 1 N NaOH. The basic aqueous layer was then extracted with dichloromethane. The organics were dried over magnesium sulfate and were concentrated. The residue was purified by flash column chromatography on silica (20% ethyl acetate in hexanes grading to ethyl acetate grading to dichloromethane) to provide 4-{5-[4-(4-Fluoro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine-1-sulfonic acid dimethylamide (0.11 g).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with 1 N NaOH
  3. extractionthe resultant mixture extracted with dichloromethane
  4. extractionThe organics were extracted with 6N HCl
  5. extractionThe basic aqueous layer was then extracted with dichloromethane
  6. dry with materialThe organics were dried over magnesium sulfate
  7. concentrationwere concentrated
  8. customThe residue was purified by flash column chromatography on silica (20% ethyl acetate in hexanes grading to ethyl acetate grading to dichloromethane)

Sources & evidence

ORD record
ord-70c175bad2ea4255868f779d054764f1
Source dataset
uspto-grants-2002_03
Patent number
US06355635B1

Reaction notes

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