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

HRID 1842915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842915
[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.[Cl:23][C:24]1[CH:25]=[C:26]([N:30]2[C:34]([CH2:35][NH2:36])=[CH:33][C:32]([C:37]([F:40])([F:39])[F:38])=[N:31]2)[CH:27]=[CH:28][CH:29]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([N:30]2[C:34]([CH2:35][NH:36][C:13]([NH:12][C:9]3[CH:8]=[CH:7][C:6]([C:2]4([OH:1])[CH2:3][O:4][CH2:5]4)=[CH:11][CH:10]=3)=[O:21])=[CH:33][C:32]([C:37]([F:38])([F:39])[F:40])=[N:31]2)[CH:27]=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 70816151(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochlorideHCID 86672148Phenyl 4-(3-hydroxyoxetan-3-yl)phenylcarbamate

Produkt 1

HCID 708161031-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)ureaAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a stirred solution of phenyl 4-(3-hydroxyoxetan-3-yl)phenylcarbamate (100 mg, 0.35 mmol, 1.0 eq) and (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (119.3 mg, 0.35 mmol, 1.0 eq) in DCM (10 mL) was added TEA (106 mg, 1.049 mmol, 3.0 eq) at RT and stirred at 40° C. overnight. The mixture was diluted with DCM (30 mL) and washed with water (10 mL), brine (10 mL) and dried over anhydrous Na2SO4 and concentrated. Crude product was purified by CC using MeOH/CHCl3 (1:9) to get 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea (100 mg; 61%) as a white solid (TLC system: MeOH/CHCl3 (1:9); Rf: 0.45).

Aufarbeitung

  1. washwashed with water (10 mL), brine (10 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customCrude product was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-63c6e07def374b28a22cb2f2aad6ed57
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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