2,6-Difluorobenzoyl isocyanate → n-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethyl}-n'-(2,6-difluorobenzoyl)urea

HRID 723607Notes

Reaction equation

HRID 723607 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH2:15])[C:10]=1[CH2:11][CH3:12].[F:22][C:23]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:24]=1[C:25]([N:27]=[C:28]=[O:29])=[O:26]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH:15][C:28]([NH:27][C:25](=[O:26])[C:24]2[C:30]([F:34])=[CH:31][CH:32]=[CH:33][C:23]=2[F:22])=[O:29])[C:10]=1[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 99233572-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethanamine

Product 1

HCID 10279117n-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethyl}-n'-(2,6-difluorobenzoyl)urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the amine of Example 43 (6.5 mg, 201 mol) in dimethylformamide (250 μL) was treated with 2,6-difluorobenzoylisocyanate (4.0 mg, 221 mol) and the mixture was shaken for 18 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-eb072272b2ee4162aa6901427e43109f
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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