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

HRID 564044ノート

反応式

HRID 564044 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6d317ded065340298f23bdd2a90c75f2
出典データセット
uspto-grants-2011_11
特許番号
US08067590B2

反応ノート

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