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2-Methoxyethanol → 1-{5-tert-Butyl-2-[4-(2-methoxy-ethoxymethyl)-phenyl]-2H-pyrazol-3-yl}-3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-urea

HRID 1174881
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Reaktionsgleichung von HRID 1174881
[C:1]([C:5]1[CH:6]=[C:7]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=3)=[CH:24][C:23]=2[F:36])=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].CS(Cl)(=O)=O.[CH3:48][O:49][CH2:50][CH2:51]O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CCOC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=3)=[CH:24][C:23]=2[F:36])=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][O:17][CH2:51][CH2:50][O:49][CH3:48])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 80192-MethoxyethanolHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 115332541-[5-tert-Butyl-2-(4-hydroxymethyl-phenyl)-2H-pyrazol-3-yl]-3-[2-fluoro-4-(2-methyl-Pyridin-4-yloxy)-phenyl)-urea

Produkt 1

HCID 11649659
1-{5-tert-Butyl-2-[4-(2-methoxy-ethoxymethyl)-phenyl]-2H-pyrazol-3-yl}-3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl]-urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-[5-tert-butyl-2-(4-hydroxymethyl-phenyl)-2H-pyrazol-3-yl]-3-[2-fluoro-4-(2-methyl-pyridin-4-yloxy)-phenyl)-urea (170 mg, 0.35 mmol) in anhydrous THF was added K2CO3 (52 mg, 0.38 mmol) followed by methanesulfonyl chloride (30 μL, 0.38 mmol). The mixture was stirred at room temperature for one day, and then 2-methoxy-ethanol (213 mg, 3.5 mmol) was added. The mixture was stirred at room temperature overnight, then EtOAc was added followed by saturated Na2CO3. The organic layer was washed with saturated Na2CO3 and brine, dried over MgSO4 and evaporated at reduced pressure. Purification by HPLC (10% to 90% aq acetonitrile afforded pure product (10 mg, 5%). 1H-NMR (CD3OD) δ 8.17 (d, J=6.0 Hz, 1H), 8.01 (t, J=9.3 Hz, 1H), 7.48-7.37 (m, 4H), 6.93-6.69 (m, 4H), 6.36 (s, 1H), 4.54 (s, 2H), 3.58 (m, 2H), 3.50 (m, 2H), 3.28 (s, 3H), 2.37 (s, 3H), 1.25 (s, 9H); MS LC-MS [M+H]+=548.1, RT=2.69 min.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. washThe organic layer was washed with saturated Na2CO3 and brine
  3. dry with materialdried over MgSO4
  4. customevaporated at reduced pressure
  5. customPurification by HPLC (10% to 90% aq acetonitrile afforded pure product (10 mg, 5%)

Quellen und Nachweise

ORD-Eintrag
ord-5c43e503b28a4c72951177286ad357ae
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07838524B2

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