4-tert-Butylbenzenesulfonamide → HCID 22282042, compound

HRID 1368632Notes

Reaction equation

HRID 1368632 reaction equation
[CH3:1][O:2][C:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([NH2:17])[N:5]([CH3:18])[N:4]=1.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29](N)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(O)C.[OH-].[Na+].Cl>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:17][C:6]2[N:5]([CH3:18])[N:4]=[C:3]([O:2][CH3:1])[C:7]=2[O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

8

Reactant 2

HCID 2228724-tert-Butylbenzenesulfonamide2×HCID 22281998HCID 22281998, compound

Product 1

HCID 22282042HCID 22282042, compoundYield 33.6%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 1049PyridineSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-methoxy-4-(2-methoxyphenoxy)-1-methyl-1H-pyrazol-5-amine (Preparation 68) (45 mg), (4-tert-butyl)benzenesulfonamide (42 mg) and 4-dimethylaminopyridine (22 mg) in dry pyridine (2 ml) was stirred at room temperature for 16 hours. A further aliquot of (4-tert-butyl)benzenesulfonamide (42 mg) was added to the reaction mixture and stirring at room temperature was continued for a further 24 hours. The reaction mixture was diluted with ethanol (2 ml) and 1.0M aqueous sodium hydroxide solution (4 ml) and was then stirred at room temperature for 4 hours. The mixture was diluted with aqueous 1.0M hydrochloric acid (20 ml) and then extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with aqueous 1.0M hydrochloric acid (20 ml), dried (magnesium sulfate) and then concentrated under vacuum. The residue was purified by chromatography on silica (5 g) using 40% ethyl acetate/pentane as eluant to give the title compound as an off-white solid (27 mg), Rf 0.85 (ethyl acetate), m.p. 187.6° C.

Workup

  1. stirringwas then stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. washThe combined organic extracts were washed with aqueous 1.0M hydrochloric acid (20 ml)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by chromatography on silica (5 g)

Sources & evidence

ORD record
ord-dcb053b6797a49d58799a8ec6cab2d7b
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

Loading…