(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 1842911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842911
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 708164601-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)ureaAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-513176fed63b4e268c9950b487b9e24d
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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