Benzaldehyde → 3-(Benzylamino)pyridazine-4-carboxylic acid

HRID 1525685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525685
[NH2:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na]>CN(C=O)C>[CH2:11]([NH:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 5360545SodiumHCID 64052513-Amino-4-pyridazinecarboxylic acid

Produkt 1

HCID 805176583-(Benzylamino)pyridazine-4-carboxylic acidAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Aminopyridazine-4-carboxylic acid (200 mg, 1.43 mmol) and benzaldehyde (0.18 mL, 1.73 mmol) were stirred in DMF (3 mL) at 90° C. for four days. The reaction mixture was allowed to cool to rt and sodium triacetoborohydride (605 mg, 2.86 mmol) was added. The reaction was stirred for 16 h. The reaction was quenched with water and extracted with EtOAc. The extracts were dried (Na2SO4) and concentrated. The residue was purified by column chromatography (0-20% MeOH/DCM). The relevant fractions were concentrated to give 6.3 mg (4%) of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 8.51 (d, 1H, 5 Hz), 7.63 (d, 1H, J=5.0 Hz), 7.30-7.39 (m, 4H), 7.22-7.25 (m, 1H), 4.72 (br s, 2H). [M+H] calc'd for C12H11N3O2, 230; found 230.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (0-20% MeOH/DCM)
  6. concentrationThe relevant fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-76b1b1284c044365857ef5201dc220f2
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085534B2

Notizen zur Reaktion

Wird geladen…