HCID 21091094, compound → HCID 21091102, compound

HRID 351237Notes

Reaction equation

HRID 351237 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:11][CH:10]=2)[N:6]([C:23]2[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[N:5]=1)([CH3:3])=[CH2:2]>C1COCC1.CO.[Pd]>[CH:1]([C:4]1[CH:8]=[C:7]([C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][CH2:15][NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[CH:11][CH:10]=2)[N:6]([C:23]2[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 21091094HCID 21091094, compound

Product 1

HCID 21091102HCID 21091102, compoundYield 57.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10% Pd-C 50% wet (20 mg) and N-(2-{4-[3-isopropenyl-1-(6-methoxy-3-pyridinyl)-1H-pyrazol-5-yl]phenoxy}ethyl)methanesulfonamide (118 mg) in THF (1 ml) and MeOH (1 ml) was hydrogenated under H2 1atm at ambient temperature for 1 day. The catalyst was removed by filtration. The filtrate and combined washings were concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by AcOEt/n-hexane=70%. The separated silica gel was extracted with 10% MeOH/CHCl3 and the solvent was evaporated in vacuo. The residue was recrystallized from AcOEt-IPE to give N-(2-{4-[3-isopropyl-1-(6-methoxy-3-pyridinyl)-1H-pyrazol-5-yl]phenoxy}ethyl)methanesulfonamide (68.6 mg) as white powder.

Workup

  1. customat ambient temperature
  2. customfor 1 day
  3. customThe catalyst was removed by filtration
  4. concentrationwere concentrated in vacuo
  5. customThe residue was purified by preparative thin layer silica gel chromatography
  6. extractionThe separated silica gel was extracted with 10% MeOH/CHCl3
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was recrystallized from AcOEt-IPE

Sources & evidence

ORD record
ord-b66df19eb81d4822a02175fb0db713d1
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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