1-(4-Methoxybenzoyl)-piperazine → (4-(2-Amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)(4-methoxyphenyl)methanone

HRID 416717

Reaktionsgleichung

Reaktionsgleichung von HRID 416717
NC1C([N+]([O-])=O)=C(N2CCN(CC(NC3SC=CN=3)=O)CC2)C(Cl)=CN=1.[NH2:27][C:28]1[C:33]([N+:34]([O-:36])=[O:35])=[C:32](Cl)[C:31]([Cl:38])=[CH:30][N:29]=1.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]([N:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[O:48])=[CH:43][CH:42]=1>C(O)(C)C>[NH2:27][C:28]1[C:33]([N+:34]([O-:36])=[O:35])=[C:32]([N:52]2[CH2:51][CH2:50][N:49]([C:47]([C:44]3[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][CH:43]=3)=[O:48])[CH2:54][CH2:53]2)[C:31]([Cl:38])=[CH:30][N:29]=1

Komponenten

5

Edukt 3

HCID 27367241-(4-Methoxybenzoyl)-piperazineHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 468678042-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

Produkt 1

HCID 57897177(4-(2-Amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)(4-methoxyphenyl)methanoneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

The method followed that used to prepare 2-[4-(2-amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide (Example 1, step 5), but using 2-amino-4,5-dichloro-3-nitropyridine (0.034 g, 0.16 mmol), isopropanol (3.0 ml), and (4-methoxyphenyl)(piperazin-1-yl)methanone (0.055 g, 0.25 mmol). Purification of the crude product on an isolute silica column using a gradient of ethyl acetate in dichloromethane as eluant (10 to 30%) afforded the title compound as a yellow solid (0.038 g, 61%). 1H-NMR (500 Mz, DMSO-d6) 3.13 (br s, 4H, piperazine N(CH2)2), 3.65 (br s, 4H, piperazine N(CH2)2), 3.86 (s, 3H, OCH3), 7.06 (d, J=8.27 Hz, 2H) and 7.47 (d, J=8.21 Hz, 2H) (2,6-C6H4—OMe and 3,5-C6H4—OMe), 7.14 (s, 2H, 2-NH2), 8.19 (s, 1H, 6-H);

Aufarbeitung

  1. customPurification of the crude product on an isolute silica column

Quellen und Nachweise

ORD-Eintrag
ord-6f5d5a0003064822bcdadcf95788e733
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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