(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine → 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(2-hydroxyethyl)phenyl)urea

HRID 1842951Notes

Reaction equation

HRID 1842951 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]1[CH:21]=[C:22]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)[CH:23]=[CH:24][C:25]=1[CH2:26][CH2:27][OH:28]>CC#N>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:30]([NH:29][C:22]2[CH:23]=[CH:24][C:25]([CH2:26][CH2:27][OH:28])=[C:20]([F:19])[CH:21]=2)=[O:31])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 58093530(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamineHCID 86672157Phenyl 3-fluoro-4-(2-hydroxyethyl)phenylcarbamate

Product 1

HCID 708158841-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(2-hydroxyethyl)phenyl)ureaYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine (synthesis described for example A141) (102 mg, 0.387 mmol, 1.0 eq) in MeCN (9 mL) was added TEA (0.214 mL, 1.55 mmol, 4.0 eq) followed by phenyl 3-fluoro-4-(2-hydroxyethyl)phenylcarbamate (108 mg, 0.395 mmol, 1.02 eq) and the mixture was stirred for 16 h at reflux. The reaction mixture was concentrated under vacuum and the residue purified by CC using EtOAc/hexane (2:1) as eluent to get 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(2-hydroxyethyl)phenyl)urea (159 mg; 92%, white solid).

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue purified by CC

Sources & evidence

ORD record
ord-85a8d0abdcc946ff8f0513d62428d96e
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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