Ethanol → HCID 178432925, Verbindung

HRID 416914

Reaktionsgleichung

Reaktionsgleichung von HRID 416914
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[N:20]=[C:21]([CH3:24])[S:22][CH:23]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.CCO.[N:28]1([C:33]2[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=2)[CH:32]=[CH:31][CH:30]=[N:29]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl.N.CN(C=O)C>[N:28]1([C:33]2[CH:40]=[CH:39][C:36]([C:37]3[NH:8][C:5]4=[N:6][CH:7]=[C:2]([Br:1])[C:3]([N:12]5[CH2:17][CH2:16][N:15]([CH2:18][C:19]6[N:20]=[C:21]([CH3:24])[S:22][CH:23]=6)[CH2:14][CH2:13]5)=[C:4]4[N:9]=3)=[CH:35][CH:34]=2)[CH:32]=[CH:31][CH:30]=[N:29]1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 27764774-(1H-Pyrazol-1-yl)benzaldehydeHCID 578971595-Bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

Produkt 1

HCID 178432925HCID 178432925, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 222AmmoniaKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a mixture of 5-bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.050 g, 0.12 mmol), EtOH (2.3 mL) and DMF (0.2 mL), 4-(1H-pyrazol-1-yl)-benzaldehyde (0.023 g, 0.13 mmol) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.36 mL, 0.36 mmol). The reaction mixture was heated at 85° C. for 24 h, then allowed to cool to room temperature and diluted with DCM and a few drops of aqueous NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH v/v 96:4 to give the title compound as a off-white solid (0.016 g, 25%); 1H-NMR (500 Mz, DMSO-d6): δ 2.63-2.71 (m, 7H), 3.65 (s, 2H, NCH2), 3.66-3.72 (m, 4H), 6.59-6.62 (m, 1H), 7.33 (s, 1H, thiazole 5-H), 7.81 (d, J=2.0 Hz, 1H), 8.03 (d, J=9.0 Hz, 2H, ArH, C6H4), 8.25 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.30 (d, J=8.5 Hz, 2H, ArH, C6H4), 8.61 (d, J=2.5 Hz, 1H), 13.54 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 3.41 min—535/537 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 535.1028, calculated for C24H24BrN8S (M+H)+: 535.1039.

Aufarbeitung

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH v/v 96:4

Quellen und Nachweise

ORD-Eintrag
ord-bb890ff0bf1b40269312377415754e96
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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