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

HRID 1847138Notes

Reaction equation

HRID 1847138 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-be7e5e93660546c3b908f85f5ca4927e
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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