Triethylamine → 1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [2-benzylamino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

HRID 930518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930518
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][C:4]([C:10]([OH:12])=O)=[CH:3]1.[CH2:13]([NH:20][C:21]1[C:22]([NH2:34])=[CH:23][CH:24]=[C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C1COCC1>[CH2:13]([NH:20][C:21]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[CH:24]=[CH:23][C:22]=1[NH:34][C:10]([C:4]1[CH:5]=[C:6]([CH3:9])[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1)=[O:12])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 218859251,5-Dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidHCID 901610111-N-benzyl-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine

Produkt 1

HCID 1178940361,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [2-benzylamino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid D1 (210.000 mg; 1.256 mmol), N2-Benzyl-4-(4-methyl-piperazin-1-yl)-benzene-1,2-diamine E-1.1 (363.000 mg; 1163.422 μmol) and triethylamine (0.435 ml; 3.141 mmol) in THF (3.000 ml) is added N-propylphosphonic acid anhydride, cyclic trimer (0.880 ml; 1.508 mmol). The mixture is stirred for 5 h at RT. The reaction is quenched with 1M NaOH, diluted with 50 ml water and extracted twice with ethyl acetate (50 ml). The combined organic layer is dried over Na2SO4 and concentrated in vacuum. The residue is used in the next step without further purification

Aufarbeitung

  1. customThe reaction is quenched with 1M NaOH
  2. additiondiluted with 50 ml water
  3. extractionextracted twice with ethyl acetate (50 ml)
  4. dry with materialThe combined organic layer is dried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue is used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-91cd0b59566b43928beb5b131df8c553
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296748B2

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