Hydrazine hydrate (1:1) → 4-aminomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one

HRID 7928

반응식

HRID 7928 반응식
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][N:13]3C(=O)C4=CC=CC=C4C3=O)=[CH:8][C:7]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([F:32])[CH:25]=3)=[N:6]2)[CH2:3][CH2:2]1.O.NN>CO>[NH2:13][CH2:12][C:9]1[C:10](=[O:11])[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:6]=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([F:32])[CH:25]=2)[CH:8]=1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 219914002-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-phthalimidomethyl-2H-pyridazin-3-one

생성물 1

HCID 98794904-aminomethyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one수율 99.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2-cyclopropylmethyl-6-(3-fluoro-4-methoxypheyl)-4-phthalimidomethyl-2H-pyridazin-3-one (190 mg, 0.43 mmol) in methanol (5 mL) was added hydrazine monohydrate (110 mg, 2.20 mmol), and the mixture was heated under reflux for 2 hours. Methanol was distilled off, and chloroform (20 mL) was added to the residue. The mixture was successively washed with water (10 mL) and brine (10 mL) in this order, and was then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by preparative thin-layer chromatography on silica gel [developing solvent: chloroform/10% w/v solution of methanol in ammonia (20/1)] to yield the title compound as yellow crystals (130 mg, 97.8%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationMethanol was distilled off
  4. additionchloroform (20 mL) was added to the residue
  5. washThe mixture was successively washed with water (10 mL) and brine (10 mL) in this order
  6. dry with materialwas then dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by preparative thin-layer chromatography on silica gel [developing solvent: chloroform/10% w/v solution of methanol in ammonia (20/1)]

출처 및 근거

ORD 기록
ord-38d2c167043c4980b48ac9206ec0428a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087606B2

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