(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine → 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(1,3-dihydroxypropan-2-yl)-3-fluorophenyl)urea

HRID 1842958Notes

Reaction equation

HRID 1842958 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].[OH:19][CH2:20][CH:21]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31](=O)[O:32]C2C=CC=CC=2)=[CH:26][C:25]=1[F:40])[CH2:22][OH:23]>CC#N>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:31]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([CH:21]([CH2:20][OH:19])[CH2:22][OH:23])=[C:25]([F:40])[CH:26]=2)=[O:32])[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 86672159Phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate

Product 1

HCID 708163281-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(1,3-dihydroxypropan-2-yl)-3-fluorophenyl)ureaYield 88.1%

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 A153) (102 mg, 0.387 mmol, 1.0 eq) in MeCN (9 mL) was added TEA (0.2145 mL, 1.55 mmol, 4.0 eq) followed by phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate (120 mg, 0.395 mmol, 1.02 eq) at RT and the mixture was stirred at reflux for 16 h. The solvent was evaporated and the crude product was purified by CC using EtOAc as eluent to get 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(1,3-dihydroxypropan-2-yl)-3-fluorophenyl)urea (162 mg; 88%).

Workup

  1. temperatureat reflux for 16 h
  2. customThe solvent was evaporated
  3. customthe crude product was purified by CC

Sources & evidence

ORD record
ord-92a1bb4eba29471b9e949e5515dfc30b
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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