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Hydrochloric Acid → N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2266390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2266390
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([O:9]CC)=O)[C:4](=[O:12])[N:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].Cl.[CH3:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([O:34][C:35]3[CH:36]=[CH:37][C:38]([NH2:41])=[N:39][CH:40]=3)=[CH:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CO.O.CN(C=O)C.CCOC(C)=O.ClCCl>[CH3:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([O:34][C:35]3[CH:36]=[CH:37][C:38]([NH:41][C:7]([C:5]4[C:4](=[O:12])[N:3]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:2]([CH3:1])[CH:6]=4)=[O:9])=[N:39][CH:40]=3)=[CH:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

12

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15192740ethyl 2,3-dihydro-1-methyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxylate
HCID 59598394
5-(7-Methoxyquinolin-4-yloxy)pyridin-2-amine

Produkt 1

HCID 44516532N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideAusbeute 20,3 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of ethyl 1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate (260 mg, 1056 μmol) in MeOH was treated with NaOH (1000 μl, 5000 μmol) in H2O (3 mL). The mixture was heated to 60° C. for 30 min and then cooled to room temperature. Then, the mixture was neutralized with aq. HCl (5 N, 1.1 mL) and concentrated to dryness. The residue was further dried with (azeotrope distillation with toluene, 3×5 mL). The resulting carboxylic acid was mixed with 5-(7-methoxyquinolin-4-yloxy)pyridin-2-amine (282 mg, 1054 μmol), Et3N (500 μl, 3587 μmol), and HATU (401 mg, 1054 μmol) in DMF (4 mL)-dichloromethane (5 mL) and was stirred at 60° C. for 2 h. Upon cooling to room temperature, the mixture was diluted with EtOAc containing 10% MeOH (30 mL) and washed with H2O. The organic layer was dried over Na2SO4, concentrated, and eluded on silica (1-10% 2N NH3-MeOH in CHCl3). The product was further purified on preparative HPLC to afford a white powder (100 mg, 20%). Calc'd for C26H21N5O4: 467.16; MS (ESI pos. ion) m/z: 468 (MH+). 1H NMR (400 MHz, DMSO-d6) 3.49 (s, 3H) 3.95 (s, 3H) 6.55 (d, J 5.1, 1H) 7.30 (dd, J 2.0, 9.0, 1H) 7.42 (s, 1H) 7.59 (s, 17H) 7.50-7.60 (m, 5H), 7.84 (dd, J 2.8, 9.2, 1H), 8.22 (d, J 9.2, 1H), 8.34-8.38 (m, 2H) 8.62 (d, J 5.3, 1H) 8.69 (s, 1H) 10.86 (s, 1H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness
  3. dry with materialThe residue was further dried with (azeotrope distillation with toluene, 3×5 mL)
  4. temperatureUpon cooling to room temperature
  5. washwashed with H2O
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe product was further purified on preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6fedb5e9a9a84be7aa5a855f2075ca8b
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07858623B2

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