Trifluoroacetic acid → N-((6-(3,5-difluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-(4-fluoropiperidin-4-yl)-1,5-naphthyridin-4-amine

HRID 2176695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176695
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH2:18][NH:19][C:20]4[CH:21]=[CH:22][N:23]=[C:24]5[C:29]=4[N:28]=[CH:27][C:26]([C:30]4(O)[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)=[CH:25]5)=[N:16][N:17]=3)[N:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.CCN(S(F)(F)[F:50])CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH2:18][NH:19][C:20]4[C:29]5[C:24](=[CH:25][C:26]([C:30]6([F:50])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]6)=[CH:27][N:28]=5)[N:23]=[CH:22][CH:21]=4)=[N:16][N:17]=3)[N:14]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 123472(Diethylamino)sulfur trifluorideHCID 57691230Tert-butyl 4-(8-((6-(3,5-difluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylamino)-1,5-naphthyridin-3-yl)-4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 44180709N-((6-(3,5-difluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-(4-fluoropiperidin-4-yl)-1,5-naphthyridin-4-amineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-(8-((6-(3,5-difluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylamino)-1,5-naphthyridin-3-yl)-4-hydroxypiperidine-1-carboxylate (30 mg, 51 μmol) in 0.5 mL of DCM was cooled to −78 C. Then added DAST (13 μl, 102 μmol) and let stir to room temperature over 30 min. TFA was then added to the reaction mixture and stirred for 30 min. The solvent was then removed by rotary evaporation and the residue was redissolved in MeOH and free based through a cation exchange column. Purification via MPLC (DCM/MeOH+1% NH4OH) yielded the title compound (15 mg, 60% yield). M/Z=491.2 [M+H], calc 490.18 for C25H21F3N8.

Aufarbeitung

  1. customThe solvent was then removed by rotary evaporation
  2. dissolutionthe residue was redissolved in MeOH
  3. customPurification via MPLC (DCM/MeOH+1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-2f8877024b8249a89621a07c1669c724
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09066954B2

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