Tetrahydrofuran → Ethyl 3-(5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate

HRID 405171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405171
CN(C([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1.[Br:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[C:46]2[CH:47]=[CH:48][C:49]([C:52]([OH:54])=O)=[N:50][CH:51]=2)=[CH:33][C:32]=1[F:55].CC[N:58]([CH:62](C)C)C(C)C>CCOC(C)=O>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[C:46]2[CH:47]=[CH:48][C:49]([C:52]([NH:58][CH2:62][CH2:26][C:27]([O:28][CH2:29][CH3:25])=[O:8])=[O:54])=[N:50][CH:51]=2)=[CH:33][C:32]=1[F:55]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 710600525-(2-(((4-Bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinic acid

Produkt 1

HCID 71059826Ethyl 3-(5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Solid HATU (227 mg, 0.60 mmol) was added to a THF solution (4.8 mL) of 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinic acid (250 mg, 0.60 mmol), i-Pr2NEt (0.31 mL, 1.79 mmol), and (3-alanine ethyl ester hydrochloride (96 mg, 0.63) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0be1920eced241659f50e3699792b44f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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