Methylamine → HCID 86711537, Verbindung

HRID 512495

Reaktionsgleichung

Reaktionsgleichung von HRID 512495
[Br:1][C:2]1[C:3](=[O:22])[C:4]([C:19]([OH:21])=O)=[CH:5][N:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH3:10])[C:7]=1[CH3:8].[CH3:23][N:24](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>CN(C=O)C.CO>[CH3:23][NH:24][C:19]([C:4]1[C:3](=[O:22])[C:2]([Br:1])=[C:7]([CH3:8])[N:6]([CH:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[CH3:10])[CH:5]=1)=[O:21]

Komponenten

7

Edukt 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867115305-Bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Produkt 1

HCID 86711537HCID 86711537, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 2b, 0.51 g, 1.41 mmol), HBTU (0.620 g, 1.64 mmol), DIPEA (0.50 mL, 2.93 mmol) in DMF (2.7 g) is stirred for 30 min. Then, methylamine (1.6 mL of 2M solution in THF, 3.20 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is diluted with MeOH and purified by preparative reversed-phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 60° C.). Yield: 0.31 g (59% of theory); ESI mass spectrum: [M+H]+=374 (bromine isotope pattern); Retention time HPLC: 0.70 min (Z011_S03).

Aufarbeitung

  1. custompurified by preparative reversed-phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 60° C.)
  2. custom0.70 min (Z011_S03)

Quellen und Nachweise

ORD-Eintrag
ord-95e64d680a1147c583a188d6ca0dfb7d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102624B2

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