Isoamyl Nitrite → HCID 9821574, compound

HRID 351252Notes

Reaction equation

HRID 351252 reaction equation
N[C:2]1[CH:6]=[C:5]([C:7]2[CH:19]=[CH:18][C:10]([O:11][CH2:12][CH2:13][NH:14][C:15]([NH2:17])=[O:16])=[CH:9][CH:8]=2)[N:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1.[Cl-:28].[Li+].N(OCCC(C)C)=O>C(#N)C.[Cu](Cl)Cl>[Cl:28][C:2]1[CH:6]=[C:5]([C:7]2[CH:19]=[CH:18][C:10]([O:11][CH2:12][CH2:13][NH:14][C:15]([NH2:17])=[O:16])=[CH:9][CH:8]=2)[N:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 433294Lithium ChlorideHCID 21091065HCID 21091065, compound

Product 1

HCID 9821574HCID 9821574, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(2-{4-[3-amino-1-(4-methoxyphenyl)-1H-pyrazol-5- yl]phenoxy}ethyl)urea 111 mg, lithium chloride 64 mg, and copper (II) chloride 81.2 mg in acetonitrile 2 ml was stirred at ambient temperature for 10 minutes. To this mixture was added isoamyl nitrite 62.3 mg, and the mixture was stirred at ambient temperature for 3 hours. The mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic layer was washed with saturated aqueous ammonium chloride solution, H2O, and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by MeOH/CHCl3=10%. The separated silica gel was extracted with 10% MeOH/CHCl3 and the solvent was evaporated in vacuo. The residue was crystallized from AcOEt/IPE to give N-(2-{4-[3-chloro-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)urea 31.1 mg as a white powder.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hours
  2. customThe mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
  3. washThe organic layer was washed with saturated aqueous ammonium chloride solution, H2O, and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer silica gel chromatography
  7. extractionThe separated silica gel was extracted with 10% MeOH/CHCl3
  8. customthe solvent was evaporated in vacuo
  9. customThe residue was crystallized from AcOEt/IPE

Sources & evidence

ORD record
ord-95e235f30fec4f7abfa92059137237de
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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