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Triethylamine → 1-(3-tert-Butyl-1-(4-cyanophenyl)-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-hydroxyethyl)-1H-indazole-5-yloxy)phenyl)methyl)urea

HRID 220224
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Reaktionsgleichung

Reaktionsgleichung von HRID 220224
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:18])OCC(Cl)(Cl)Cl)[N:7]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][CH2:27][C:28]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:29]=1[O:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH2:40][CH2:41][OH:42])[N:35]=[CH:34]2.C([N:50](CC)CC)C>CC(N(C)C)=O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:26][CH2:27][C:28]2[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:29]=2[O:30][C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[N:36]([CH2:40][CH2:41][OH:42])[N:35]=[CH:34]3)=[O:18])[N:7]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[N:50])=[CH:23][CH:24]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 445421222-(5-(2-(Aminomethyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethanol

Produkt 1

HCID 687836801-(3-tert-Butyl-1-(4-cyanophenyl)-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-hydroxyethyl)-1H-indazole-5-yloxy)phenyl)methyl)ureaAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

2,2,2-Trichloroethyl 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-ylcarbamate (0.22 g, 0.529 mmol), 2-(5-(2-(aminomethyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethanol (prepared as in Example 1, Steps E1-E6; 0.175 g, 0.582 mmol), and triethylamine were combined in a minimal amount of DMA and stirred at ambient temperature overnight. The reaction mixture was concentrated, and the residue was diluted with DCM. The DCM was washed with aqueous NH4Cl and aqueous Na2CO3. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography, eluting with 1% MeOH in ethyl acetate to provide 100 mg (32.6%) of the desired product. MS M+1 (568).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with DCM
  3. washThe DCM was washed with aqueous NH4Cl and aqueous Na2CO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 1% MeOH in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8b01769cc7eb4309a298211f140dc960
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202899B2

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