(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-(3-fluoro-4-(1-hydroxycyclopropyl)phenyl)urea

HRID 1842906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842906
Cl.[C:2]([C:6]1[CH:10]=[C:9]([CH2:11][NH2:12])[N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[N:7]=1)([CH3:5])([CH3:4])[CH3:3].[F:20][C:21]1[CH:22]=[C:23]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)[CH:24]=[CH:25][C:26]=1[C:27]1([OH:30])[CH2:29][CH2:28]1>CC#N>[C:2]([C:6]1[CH:10]=[C:9]([CH2:11][NH:12][C:32]([NH:31][C:23]2[CH:24]=[CH:25][C:26]([C:27]3([OH:30])[CH2:28][CH2:29]3)=[C:21]([F:20])[CH:22]=2)=[O:33])[N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[N:7]=1)([CH3:5])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 70816240(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine hydrochlorideHCID 86672145Phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamate

Produkt 1

HCID 708160711-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(1-hydroxycyclopropyl)phenyl)ureaAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of (3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine hydrochloride (synthesis described for example A106) (0.104 mg, 0.348 mmol, 1.0 eq) in MeCN (8 mL) was added TEA (0.193 mL, 1.39 mmol, 4.0 eq) followed by addition of phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamate (0.10 mg, 0.355 mmol, 1.02 eq) at RT and the mixture was stirred at reflux overnight. The solvents were evaporated and the crude product was purified by CC (eluent EtOAc/cyclohexane 1:2) to get 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(1-hydroxycyclopropyl)phenyl)urea (104 mg; 65%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e34263f1f62944ecb253b2c13e3002da
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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