(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-(3-hydroxyazetidin-1-yl)phenyl)urea

HRID 1842997Notes

Reaction equation

HRID 1842997 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:31][C:32](=O)[O:33]C2C=CC=CC=2)[CH:23]=[CH:24][C:25]=1[N:26]1[CH2:29][CH:28]([OH:30])[CH2:27]1>C(#N)C>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:32]([NH:31][C:22]2[CH:23]=[CH:24][C:25]([N:26]3[CH2:27][CH:28]([OH:30])[CH2:29]3)=[C:20]([F:19])[CH:21]=2)=[O:33])[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 86672171Phenyl 3-fluoro-4-(3-hydroxyazetidin-1-yl)phenylcarbamate

Product 1

HCID 708165051-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl)ureaYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine (106 mg, 0.398 mmol, 1.0 eq) in acetonitrile (9 mL) was added TEA (0.22 mL, 1.6 mmol, 4.0 eq) followed by phenyl 3-fluoro-4-(3-hydroxyazetidin-1-yl)phenylcarbamate (122 mg, 0.406 mmol, 1.02 eq) and the mixture was stirred at reflux for 16 h. The reaction mixture was evaporated and the residue was purified by CC (EtOAc/n-hexane 2:1 as eluent) to obtain 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl)urea (183 mg; 97%).

Workup

  1. temperatureat reflux for 16 h
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by CC (EtOAc/n-hexane 2:1 as eluent)

Sources & evidence

ORD record
ord-a561e8caad654b14b021ef5c9d43b0f2
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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