Sodium Dithionite → 6-Bromo-2-(4-methoxyphenyl)-7-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridine

HRID 416781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416781
BrC1C(N2CCN(C(NC3C=CC=CC=3)=O)CC2)=C2N=C(C3C=CC(N(C)C)=CC=3)NC2=NC=1.[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH:52]([C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)[CH3:53])[CH2:48][CH2:47]2)=[C:38]([N+:43]([O-])=O)[C:39]([NH2:42])=[N:40][CH:41]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH3:68][O:69][C:70]1[CH:75]=[CH:74][C:73]([CH:76]=O)=[CH:72][CH:71]=1>CN(C=O)C>[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH:52]([C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)[CH3:53])[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:76]([C:73]3[CH:74]=[CH:75][C:70]([O:69][CH3:68])=[CH:71][CH:72]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Komponenten

6

Edukt 4

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 468683495-Bromo-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, Verbindung

Produkt 1

HCID 1784888896-Bromo-2-(4-methoxyphenyl)-7-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

This was prepared using the same procedure as for 4-(6-bromo-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)-N-phenylpiperazine-1-carboxamide, but here using 5-bromo-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amine (30 mg, 0.074 mmol), DMF (1 mL), 1M Na2S2O4 (3 eq, 0.22 mmol, 0.22 mL) and 4-methoxybenzene carboxaldehyde (1.05 eq, 0.077 mmol, 0.0096 mL). After 16 h, filtration of the precipitate and washing with ethanol (1 mL) and cold water (1 mL) gave the product (15 mg, 42%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.37 (d, J=6.7 Hz, 3H, CHCH3), 2.56-2.65 (2 m, 4H, piperazine N(CH2)2), 3.58 (q, J=6.9 Hz, 1H, CHCH3), 3.66 (br s, 4H, piperazine N(CH2)2), 3.85 (s, 3H, OCH3), 7.11 (d, J=8.8 Hz, 2H, methoxyphenyl), 7.40 (d, J=5.4 Hz, 2H, pyridine H-3 & H-5), 8.14 (d, J=8.5 Hz, 2H, methoxyphenyl), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.55 (d, J=5.4 Hz, 2H, pyridine H-2 & H-6), 13.40 (br s, 1H, imidazo[4,5-b]pyridine NH);

Aufarbeitung

  1. customThis was prepared
  2. filtrationfiltration of the precipitate
  3. washwashing with ethanol (1 mL) and cold water (1 mL)

Quellen und Nachweise

ORD-Eintrag
ord-707de391bbea4e78b31fee44f4512e0b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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