Ethyl 3-{3-t-butyl-5-[3-(4-chlorophenyl)ureido]-1h-pyrazol-1-yl}benzoate → 1-{5-t-Butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2h-pyrazol-3-yl}-3-(4-chloro-phenyl)-urea

HRID 16979

Reaktionsgleichung

Reaktionsgleichung von HRID 16979
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:12])[N:7]([C:21]2[CH:22]=[C:23]([CH:29]=[CH:30][CH:31]=2)C(OCC)=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Mg]Br.[C:35]1([CH3:41])C=CC=C[CH:36]=1.C1C[O:45]CC1>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:12])[N:7]([C:21]2[CH:31]=[CH:30][CH:29]=[C:23]([C:35]([OH:45])([CH3:41])[CH3:36])[CH:22]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 21867337Ethyl 3-{3-t-butyl-5-[3-(4-chlorophenyl)ureido]-1h-pyrazol-1-yl}benzoateHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 184498651-{5-t-Butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2h-pyrazol-3-yl}-3-(4-chloro-phenyl)-ureaAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of Example C (220 mg, 0.5 mmol) in dry THF (20 mL) was added dropwise a solution of methyl magnesium bromide in toluene/THF (3.6 mL, 5.0 mmol) at −78° C. under N2. After stirring for 1 h, the mixture was allowed to rise to RT and stirred for another 2 h. The reaction mixture was quenched with saturated NH4Cl and aqueous HCl solution (10%), and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), the solvent was removed in vacuo and the residue was purified by column chromatography to afford 1-{5-t-butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-pyrazol-3-yl}-3-(4-chloro-phenyl)-urea (174 mg, 81%). 1H NMR (DMSO-d6): 9.11 (s, 1H), 8.34 (s, 1H), 7.59 (s, 1H), 7.46 (t, J=8.8 Hz, 1H), 7.43-7.40 (m, 3H), 7.31-7.28 (m, 3H), 6.34 (s, 1H), 5.13 (s, 1H), 1.42 (s, 6H), 1.27 (s, 9H); MS (ESI) m/z: 428 (M+H+).

Aufarbeitung

  1. customto rise to RT
  2. stirringstirred for another 2 h
  3. customThe reaction mixture was quenched with saturated NH4Cl and aqueous HCl solution (10%)
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7c74fbbe13be42449700741559708bbe
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737283B2

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