Isopropylamine → 6-{(E)-2-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-vinyl}-N-isopropyl-nicotinamide

HRID 402419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402419
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2/[CH:14]=[CH:15]/[C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=2)=[CH:4][CH:3]=1.CN(C(O[N:33]1N=N[C:35]2C=CC=[CH:39][C:34]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(N)(C)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2/[CH:14]=[CH:15]/[C:16]2[CH:24]=[CH:23][C:19]([C:20]([NH:33][CH:34]([CH3:39])[CH3:35])=[O:21])=[CH:18][N:17]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 674980266-{(E)-2-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-vinyl}-nicotinic acid

Produkt 1

HCID 573352606-{(E)-2-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazol-4-yl]-vinyl}-N-isopropyl-nicotinamideAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-{(E)-2-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-vinyl}-nicotinic acid (49 mg, 0.15 mmol) and TBTU (53 mg, 0.17 mmol) in DMF (0.8 mL) was added DIPEA (129 μL, 0.76 mmol). Then isopropylamine (14 μL, 0.17 mmol) was added and the mixture was stirred at room temperature under Ar for 1 h. The mixture was then evaporated and purification by chromatography (silica, 0 to 10% methanol in dichloromethane) afforded the title compound (45 mg, 82%) as a light yellow solid after recrystallisation from methanol/water. MS: m/e=366.1 [M+H]+.

Aufarbeitung

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 0 to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-08de9a53146641509c4530cd998c55f8
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742097B2

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