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

HRID 723606Notes

Reaction equation

HRID 723606 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, 201 mol) 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-eb02d140c24a4f8ab74bfb694b4b3e19
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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