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Nitrogen → 1-(2-Hydroxy-2-methylpropyl)-N-(4-(5-isoquinolinyl)-3-methylphenyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2356353
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Reaktionsgleichung

Reaktionsgleichung von HRID 2356353
[CH:1]1[C:10]2[C:5](=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[C:25](=[O:41])[N:26]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:27]([CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])[C:28]=2[CH3:29])=[O:23])=[CH:17][C:16]=1[CH3:42].C([O-])(O)=O.[Na+].N#N>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O1CCOCC1>[OH:34][C:31]([CH3:33])([CH3:32])[CH2:30][N:27]1[C:28]([CH3:29])=[C:24]([C:22]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)=[C:16]([CH3:42])[CH:17]=2)=[O:23])[C:25](=[O:41])[N:26]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
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Komponenten

7

Edukt 4

HCID 947NitrogenHCID 516892Sodium BicarbonateHCID 599474Isoquinoline-5-boronic acidHCID 59383945N-(4-bromo-3-methylphenyl)-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Produkt 1

HCID 249989631-(2-Hydroxy-2-methylpropyl)-N-(4-(5-isoquinolinyl)-3-methylphenyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A sealable tube was charged with PdCl2(dppf)-CH2Cl2 adduct (0.013 g, 0.016 mmol), isoquinolin-5-ylboronic acid (0.057 g, 0.33 mmol), N-(4-bromo-3-methylphenyl)-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (0.150 g, 0.33 mmol) and 4 mL dioxane. To this mixture, NaHCO3 solution (0.49 ml, 0.98 mmol) was added and the reaction mixture blanket with N2. The vessel was sealed and heated at 80 C for 19 h. The mixture was allowed to cool to rt, filtered through a pad of celite using ethyl acetate as the eluent and the organic layer washed with water, brine, dried over Na2SO4, filtered and evaporated. The mixture was purified via flash chromatography using a mixture of MeOH in EtOAc as the eluent. The title compound was isolated as an off-white solid (80 mg). MS (ESI pos. ion) m/z=507 (MH+). Calc'd mass for C31H30FN4O3: 506.60. 1H NMR (400 MHz, dmso-d6) δ 10.86 (s, 1H), 9.39 (s, 1H), 8.45 (d, J=5.9 Hz, 1H), 8.17 (d, J=8.1 Hz, 1H), 7.74-7.80 (m, 1H), 7.56-7.85 (m, 5H), 7.44-7.50 (m, 1H), 7.37 (d, J=7.7 Hz, 2H), 7.25 (d, J=5.8 Hz, 1H), 7.17 (d, J=8.1 Hz, 1H), 3.31 (s, 2H), 2.82 (s, 3H), 1.95 (s, 3H), 0.98 (s, 6H).

Aufarbeitung

  1. customThe vessel was sealed
  2. temperatureheated at 80 C for 19 h
  3. filtrationfiltered through a pad of celite
  4. washthe organic layer washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe mixture was purified via flash chromatography
  9. additiona mixture of MeOH in EtOAc as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-332db742bbcc4f4a93efc74d30daf657
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759344B2

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