Water → HCID 21091125, compound

HRID 351275Notes

Reaction equation

HRID 351275 reaction equation
[C:1]([C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[CH:10][CH:9]=2)[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:4]=1)#[N:2].CC[N:26]([CH2:29]C)CC.[OH2:31].C(Cl)(Cl)Cl>C(Cl)Cl>[C:1]([C:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][NH:15][C:29]([NH2:26])=[O:31])=[CH:12][CH:13]=2)[N:5]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 8471TriethylamineHCID 21090862HCID 21090862, compound

Product 1

HCID 21091125HCID 21091125, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-cyano-1-(4-methoxyphenyl)-5-[4-(aminometyl)phenyl]-1H-pyrazole (90 mg) trimethylsilylisocyanate (152 mg) and Et3N (0.18 ml) in CH2Cl2 (5 ml) was stirred at room temperature. After stirring for 5 hours (checked by TLC), water and CHCl3 was added. The organic layer was separated. Aqueous layer was extracted with EtOAc. The combined organic layer was washed with water and brine. Dried over MgSO4, filtered and evaporated under reduced pressure to give 48 mg (52%) of N-{4-[3-cyano-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]benzyl}urea.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionAqueous layer was extracted with EtOAc
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9d587916c6fd41df8a070fdc86d57beb
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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