Phenyl isocyanatoformate → [4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]methyl phenyl imidodicarbonate

HRID 353082Notes

Reaction equation

HRID 353082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][C:6]1[C:7]([CH2:15][CH3:16])=[N:8][N:9]([CH2:13][OH:14])[C:10]=1[CH2:11][CH3:12].[N:21]([C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25])=[C:22]=[O:23]>CN(C)C=O>[C:22]([NH:21][C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25])([O:14][CH2:13][N:9]1[C:10]([CH2:11][CH3:12])=[C:6]([CH2:5][C:4]2[CH:17]=[C:18]([Cl:20])[CH:19]=[C:2]([Cl:1])[CH:3]=2)[C:7]([CH2:15][CH3:16])=[N:8]1)=[O:23]

Participants

4

Reactant 2

HCID 4148962Phenyl isocyanatoformateHCID 9857970[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]methanol

Product 1

HCID 10277209[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]methyl phenyl imidodicarbonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the alcohol of Example 41 (6.3 mg, 20 μmol) in dimethylformamide (250 μL) was treated with phenyl isocyanatoformate (3.6 mg, 22 μmol) and the mixture was shaken for 1.5 hours. The reaction mixture was filtered and the filtrate was purified by HPLC (Hypersil Thermoquest Luna C8 150×10 mm column; a gradient mobile phase was used, 10:90 (by volume)→95:5 (by volume) acetonitrile:(water, 95% by volume/trifluoroacetic acid, 0.1% by volume/acetonitrile 5%, by volume)).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was purified by HPLC (Hypersil Thermoquest Luna C8 150×10 mm column

Sources & evidence

ORD record
ord-4842fff2a6144d74b0dcf0595f34b224
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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