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

HRID 1847138노트

반응식

HRID 1847138 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-be7e5e93660546c3b908f85f5ca4927e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952151B2

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