Sodium Acetate → [6-(2-Methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1853963

Reaktionsgleichung

Reaktionsgleichung von HRID 1853963
CN([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[CH3:21])[CH2:6]1)C.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH2:38])=[NH:37])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:21][C:13]1[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=1[N:7]1[CH2:8][CH2:9][C:10]2[N:37]=[C:36]([NH:35][C:32]3[CH:31]=[CH:30][C:29]([N:26]4[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]4)=[CH:34][CH:33]=3)[N:38]=[CH:4][C:5]=2[CH2:6]1

Komponenten

6

Edukt 3

HCID 517045Sodium AcetateHCID 673288983-Dimethylaminomethylene-1-(2-methyl-5-nitrophenyl)piperidin-4-oneHCID 1784807471-(4-(4-Methylpiperazin-1-yl)phenyl)guanidine

Produkt 1

HCID 67328470[6-(2-Methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 3-Dimethylaminomethylene-1-(2-methyl-5-nitrophenyl)-piperidin-4-one (12.06 gm, 41.7 mmol)[as prepared in reference 1] in Ethanol (250 ml) were added N-[4-(4-Methyl-piperazin-1-yl)-phenyl]-guanidine (38.9 gm, 167 mmol) and sodium acetate (27.32 gm, 334 mmol) and solution was heated under reflux for 12 hours. After cooling to room temperature, the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was washed with brine, dried [sodium sulfate] and concentrated under vacuum. The crude product obtained was further purified by silica gel chromatography using 5-10% Methanol/Chloroform as eluent to give pure desired product [47] i.e., [6-(2-Methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine as yellow solid. (Yield: 3.65 gm, 19.0%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried [sodium sulfate]
  6. concentrationconcentrated under vacuum
  7. customThe crude product obtained
  8. customwas further purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb10d4bf5efb4a6e97b20e7f3b19818a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962637B2

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