Hydrochloric Acid → HCID 86612531, compound

HRID 351271Notes

Reaction equation

HRID 351271 reaction equation
[CH:1]([Mg]Br)([CH3:3])[CH3:2].CON(C)[C:9]([C:11]1[CH:15]=[C:14]([C:16]2[CH:30]=[CH:29][C:19]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:18][CH:17]=2)[N:13]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[N:12]=1)=[O:10].Cl>C1COCC1>[C:9]([C:11]1[CH:15]=[C:14]([C:16]2[CH:30]=[CH:29][C:19]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:18][CH:17]=2)[N:13]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[N:12]=1)(=[O:10])[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86612532HCID 86612532, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 86612531HCID 86612531, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 0.76M solution of isopropyl magnesium bromide in THF (8.5 ml) was added dropwise to a solution of tert-butyl {4-[3-{[methoxy(methyl)amino]carbonyl}-1-(4-methoxy-phenyl)-1-H-pyrazol-5-yl]benzyl}carbamate (1 g) in THF (10 ml) at 10–15° C. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was poured into a mixture of 1M HCl and ice. The mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=20%, 25%, then 10% MeOH/CHCl3. The combined pure fraction was concentrated in vacuo to give tert-butyl {4-[3-isobutyryl-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]benzyl}carbamate (318 mg) as an amorphous powder.

Workup

  1. extractionThe mixture was extracted with AcOEt
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with AcOEt/n-hexane=20%, 25%
  7. concentrationThe combined pure fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-c5b91f0159db4f668919437d35b72891
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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