Triethylamine → 1-Benzyl-N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxamide

HRID 2359681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2359681
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([N:32]1[N:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]2=[C:34]([C:41]([OH:43])=O)[C:33]1=[O:44])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:45][O:46][C:47]1[CH:56]=[C:55]2[C:50]([C:51]([O:57][C:58]3[CH:59]=[CH:60][C:61]([NH2:64])=[N:62][CH:63]=3)=[CH:52][CH:53]=[N:54]2)=[CH:49][CH:48]=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.O>[CH2:25]([N:32]1[N:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]2=[C:34]([C:41]([NH:64][C:61]2[CH:60]=[CH:59][C:58]([O:57][C:51]3[C:50]4[C:55](=[CH:56][C:47]([O:46][CH3:45])=[CH:48][CH:49]=4)[N:54]=[CH:53][CH:52]=3)=[CH:63][N:62]=2)=[O:43])[C:33]1=[O:44])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595983945-(7-Methoxyquinolin-4-yloxy)pyridin-2-amineHCID 666194781-Benzyl-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxylic acid

Produkt 1

HCID 119631431-Benzyl-N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of HATU (760 mg, 2.0 mmol), crude 1-benzyl-2-oxo-1,2-dihydropyrazolo[1,5-a]pyridine-3-carboxylic acid (268 mg, 1.0 mmol), 5-(7-methoxyquinolin-4-yloxy)pyridin-2-amine (220 mg, 1.0 mmol), and triethylamine (2000 μl, 14 mmol) in DMF (3 mL) plus CHCL3 (3 mL) was stirred at 60° C. for 4 days. Then, the mixture was diluted with EtOAc (10 mL) and H2O (5 mL). The organic layer was washed with NaOH (1 N), H2O, NaHCO3, and dried over Na2SO4. The organic residue was purified on silica and further purified by trituration with EtOAc in ether (5%), resulting a light green powder. Calc'd for C30H23N5O4: 517; MS (ESI pos. ion) m/z: 518 1HNMR (CDCl3, 400 MHz): 10.96 (1H, s), 8.62 (1H, d, J 5.3), 8.48 (1H, d, J 9.0), 8.29-8.25 (2H, m), 7.73 (1H, d, J 6.8), 7.55-7.53 (1H, dd, J 2.7, 9.0), 7.48-7.43 (2H, m), 7.40-7.34 (3H, m), 7.29-7.23 (3H, m), 6.74 (1H, t, J 7.1), 6.46 (1H, d J 5.3), 5.48 (2H, s), 3.98 (3H, s).

Aufarbeitung

  1. washThe organic layer was washed with NaOH (1 N), H2O, NaHCO3
  2. dry with materialdried over Na2SO4
  3. customThe organic residue was purified on silica
  4. customfurther purified by trituration with EtOAc in ether (5%)
  5. customresulting a light green powder

Quellen und Nachweise

ORD-Eintrag
ord-28b148e429344bbcbd1dd654197c7a47
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685983B2

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