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1,1'-Carbonyldiimidazole → 1-[5-tert-butyl-2-(4-nitrophenyl)-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]urea

HRID 1174854
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1174854
[C:1]([C:5]1[CH:6]=[C:7]([NH2:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:25]([N:27]2C=N[CH:29]=[CH:28]2)=[O:26])C=1.[N:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]2[CH:44]=CC(N)=[CH:41][CH:40]=2)=[CH:34][CH:33]=1>ClCCCl>[C:1]([C:5]1[CH:6]=[C:7]([NH:19][C:25]([NH:27][C:28]2[CH:29]=[CH:44][C:39]([O:38][C:35]3[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=3)=[CH:40][CH:41]=2)=[O:26])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13023603-tert-butyl-1-(4-nitrophenyl)-1H-pyrazol-5-amineHCID 115645894-(Pyridin-4-yloxy)aniline

Produkt 1

HCID 536301901-[5-tert-butyl-2-(4-nitrophenyl)-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]ureaAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 5-tert-butyl-2-(4-nitrophenyl)-2H-pyrazol-3-ylamine (5.0 g, 19.2 mmol) in anhydrous DCE (2 mL) was added CDI (3.5 g, 21.1 mmol), and the reaction was stirred under N2 at room temperature for 18 h. 4-(Pyridin-4-yloxy)phenylamine (3.3 g, 17.7 mmol, Dumas et al., U.S. pat. appl. US2002065296 (2002)) in DCE (12 mL) was added to the reaction, and the solution was stirred under N2 at room temperature for 7 h. The reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The crude residue was purified by MPLC (1:1 hexanes/EtOAc) to give 5.6 g (68%) of the desired product. 1H-NMR (DMSO-d6) δ 9.21 (s, 1H), 8.68 (s, 1H), 8.43 (d, J=6.3 Hz, 2H), 8.36 (d, J=7.2 Hz, 2H), 7.90 (d, J=6.9 Hz, 2H), 7.50 (d, J=6.9 Hz, 2H), 7.09 (d, J=6.6 Hz, 2H), 6.86 (d, J=5.7 Hz, 2H), 6.44 (s, 1H), 1.29 (s, 9H); MS LC-MS [M+H]+=473, RT=2.60 min.

Aufarbeitung

  1. stirringthe solution was stirred under N2 at room temperature for 7 h
  2. customThe reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customThe crude residue was purified by MPLC (1:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-0c8ff0e44252459cb3ad7af55e9dc1cd
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07838524B2

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