(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine hydrochloride → 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea

HRID 1842911Notes

Reaction equation

HRID 1842911 reaction equation
[OH:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:21])OC3C=CC=CC=3)=[CH:8][CH:7]=2)[CH2:5][O:4][CH2:3]1.Cl.[C:23]([C:27]1[CH:31]=[C:30]([CH2:32][NH2:33])[N:29]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=2)[N:28]=1)([CH3:26])([CH3:25])[CH3:24]>CC#N>[C:23]([C:27]1[CH:31]=[C:30]([CH2:32][NH:33][C:13]([NH:12][C:9]2[CH:8]=[CH:7][C:6]([C:2]3([OH:1])[CH2:3][O:4][CH2:5]3)=[CH:11][CH:10]=2)=[O:21])[N:29]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=2)[N:28]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 70816240(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine hydrochlorideHCID 86672148Phenyl 4-(3-hydroxyoxetan-3-yl)phenylcarbamate

Product 1

HCID 708164601-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)ureaYield 61.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of phenyl 4-(3-hydroxyoxetan-3-yl)phenylcarbamate (synthesis described for example A108) (97 mg, 0.34 mmol, 1.02 eq) and (3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine hydrochloride (100 mg, 0.33 mmol, 1.0 eq) in MeCN (8 mL) was added TEA (0.185 mL, 1.33 mmol, 4.0 eq) at RT and the mixture stirred at reflux overnight. The solvents were evaporated and the crude product was purified by CC (EtOAc/cyclohexane 3:2 as eluent) to get 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea (92 mg; 61%).

Workup

  1. customat RT
  2. temperatureat reflux overnight
  3. customThe solvents were evaporated
  4. customthe crude product was purified by CC (EtOAc/cyclohexane 3:2 as eluent)

Sources & evidence

ORD record
ord-513176fed63b4e268c9950b487b9e24d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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