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

HRID 1525685ノート

反応式

HRID 1525685 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 805176583-(Benzylamino)pyridazine-4-carboxylic acid収率 4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-76b1b1284c044365857ef5201dc220f2
出典データセット
uspto-grants-2015_07
特許番号
US09085534B2

反応ノート

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