Triethylamine → 5-Hydroxy-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

HRID 564044노트

반응식

HRID 564044 반응식
Cl[C:2]1[C:3](=[O:15])[N:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[N:5]=[CH:6][C:7]=1[OH:8].C(N(CC)CC)C>CO.[Pd]>[OH:8][C:7]1[CH:6]=[N:5][N:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[C:3](=[O:15])[CH:2]=1

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 547041594-Chloro-5-hydroxy-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

생성물 1

HCID 579503555-Hydroxy-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To 14.3 g (62.0 mmol) 4-chloro-5-hydroxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one in 200 mL MeOH and 8.71 mL (62.0 mmol) triethylamine is added 5.00 g 10% Pd/C. The reaction mixture is stirred under a hydrogen atmosphere of 1700 hPa at RT for 16 h. The catalyst is removed by filtration and the solvent is evaporated. 200 mL water is added to the residue, the precipitate is collected, washed with water and dried (fraction A, 7.80 g). The aqueous phase is concentrated and the residue is directly added to a reverse HPLC for purification (Waters xbridge; water (0.15% NH4OH)/acetonitril 95:5 to 10:90) to afford fraction B (4.2 g) which is combined with fraction A.

후처리

  1. customThe catalyst is removed by filtration
  2. customthe solvent is evaporated
  3. addition200 mL water is added to the residue
  4. customthe precipitate is collected
  5. washwashed with water
  6. customdried (fraction A, 7.80 g)
  7. concentrationThe aqueous phase is concentrated
  8. additionthe residue is directly added to a reverse HPLC for purification (Waters xbridge; water (0.15% NH4OH)/acetonitril 95:5 to 10:90)
  9. customto afford fraction B (4.2 g) which

출처 및 근거

ORD 기록
ord-6d317ded065340298f23bdd2a90c75f2
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067590B2

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