(1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride → 1-((1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea

HRID 1842893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842893
Cl.[Cl:2][C:3]1[C:4]([O:20][CH3:21])=[C:5]([N:9]2[C:13]([CH2:14][NH2:15])=[CH:12][C:11]([C:16]([F:19])([F:18])[F:17])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[F:22][C:23]1[CH:24]=[C:25]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)[CH:26]=[CH:27][C:28]=1[CH2:29][OH:30]>C(Cl)Cl.O>[Cl:2][C:3]1[C:4]([O:20][CH3:21])=[C:5]([N:9]2[C:13]([CH2:14][NH:15][C:32]([NH:31][C:25]3[CH:26]=[CH:27][C:28]([CH2:29][OH:30])=[C:23]([F:22])[CH:24]=3)=[O:33])=[CH:12][C:11]([C:16]([F:18])([F:19])[F:17])=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 70816406(1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochlorideHCID 86672140Phenyl (3-fluoro-4-(hydroxymethyl)phenyl)carbamate

Produkt 1

HCID 708164171-((1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)ureaAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (100 mg, 0.38 mmol, 1.0 eq) in DCM (5 mL) was added TEA (0.16 mL, 1.14 mmol, 3.0 eq) followed by phenyl 3-fluoro-4-(hydroxymethyl)phenyl-carbamate (131 mg, 0.38 mmol, 1.0 eq) at RT and stirred for 16 h. The reaction mixture was diluted with water (15 mL), extracted with DCM (2×15 mL). The combined organic layer was washed with brine (15 mL), dried over anhydrous Na2SO4 and evaporated under vacuum. Crude product was purified by CC to get 1-((1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea (110 mg; 61%) as off white solid (TLC system: MeOH/CHCl3 (1:9); Rf: 0.55).

Aufarbeitung

  1. extractionextracted with DCM (2×15 mL)
  2. washThe combined organic layer was washed with brine (15 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. customCrude product was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-14a7354c6b4d4d88a6c6ad52197177bd
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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