Methanol → 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(4-pyrrolo[3,2-c]pyridin-1-yl-naphthalen-1-yl)-urea

HRID 2417001

Reaktionsgleichung

Reaktionsgleichung von HRID 2417001
C1(O[C:8](=[O:26])[NH:9][C:10]2[N:11]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[N:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:14]=2)C=CC=CC=1.[NH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([N:38]2[C:46]3[CH:45]=[CH:44][N:43]=[CH:42][C:41]=3[CH:40]=[CH:39]2)=[CH:30][CH:29]=1.CO>CS(C)=O.ClCCl>[C:15]([C:13]1[CH:14]=[C:10]([NH:9][C:8]([NH:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([N:38]3[C:46]4[CH:45]=[CH:44][N:43]=[CH:42][C:41]=4[CH:40]=[CH:39]3)=[CH:30][CH:29]=2)=[O:26])[N:11]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[N:12]=1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 11057211phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamateHCID 114823371-(4-Aminonaphthalen-1-yl)pyrrolo[3,2-c]pyridine

Produkt 1

HCID 101646921-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(4-pyrrolo[3,2-c]pyridin-1-yl-naphthalen-1-yl)-ureaAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester (144 mg, 0.411 mmol, 1.1 equiv.) and 1-(4-aminonaphthalen-1-yl)pyrrolo[3,2-c]pyridine (Example 1) (97 mg, 0.374 mmol, 1 equiv.) were combined in 2 mL anhydrous DMSO. The mixture was stirred under inert atmosphere for 1.5 h, then heated to 60° C. for 0.5 h. The reaction was allowed to cool, quenched with 5% aqueous NaOH and extracted with EtOAc three times. The combined organic extracts were washed with water, then brine. They were then dried (MgSO4), filtered, and the solvents were removed in vacuo. The residue was purified by column chromatography using 3-4% MeOH in dichloromethane providing 161 mg title compound (0.313 mmol, 84%) as a glassy solid.

Aufarbeitung

  1. temperatureto cool
  2. customquenched with 5% aqueous NaOH
  3. extractionextracted with EtOAc three times
  4. washThe combined organic extracts were washed with water
  5. dry with materialThey were then dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8219aef5193941dd8d185effa8f46b84
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825184B2

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