Ibudilast → Ibudilast

HRID 731694

反応式

HRID 731694 の反応式
[CH:1]([C:4]1[C:12]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[I-].N[N+]1C=CC=CC=1C.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(OC(=O)C(C)C)(=O)C(C)C.C(OCC)(=O)C.O>[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[CH:1]([C:4]1[C:12]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

参加物

9

反応物 4

HCID 3671IbudilastHCID 11430Potassium Carbonate3 回HCID 14798Sodium HydroxideHCID 122915071-Amino-2-methylpyridinium Iodide

生成物 2

HCID 3671Ibudilast収率 51.3%HCID 113786582-Isopropylpyrazolo[1,5-a]pyridine収率 32.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 7346Isobutyric anhydride溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one. The dry salt (113 g) from Example 1 (a) was suspended in isobutyric anhydride (515 g) in a large round bottom flask equipped with a mechanical stirrer and K2CO3 (85 g) was added with stirring. The mixture was refluxed for 8 hours, cooled to room temperature and water (10 ml) was added followed by addition of K2CO3 (10 g) in portions. After the initial vigorous reaction subsided, water (500 ml) and ethyl acetate (500 ml) were added, followed by 280 g of K2CO3, added in portions with continuous mechanical stirring to control foaming. The reaction mixture was stirred for 1 hour at room temperature, 50 mL of 50% NaOH was added, and the mixture extracted with ethyl acetate (4×250 ml). Evaporation of the solution yielded a viscous oil, which was distilled under high vacuum to provide 25.2 g (32.9%) of 2-isopropylpyrazolo[1,5-a]pyridine (b.p. 45-75° C./0.25-0.5 mm Hg), and 60.4 g (51.3%) of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one (b.p. 125-135° C./0.1 mm Hg; m.p. 53-55° C.) (T. Irikura, et al., U.S. Pat. No. 3,850,941, Nov. 26, 1974). Compound 411.

後処理

  1. customequipped with a mechanical stirrer
  2. temperatureThe mixture was refluxed for 8 hours
  3. customAfter the initial vigorous reaction
  4. additionadded in portions with continuous
  5. stirringmechanical stirring
  6. stirringThe reaction mixture was stirred for 1 hour at room temperature
  7. extractionthe mixture extracted with ethyl acetate (4×250 ml)
  8. customEvaporation of the solution
  9. customyielded a viscous oil, which
  10. distillationwas distilled under high vacuum

出典と根拠

ORDレコード
ord-fc5801f80e854c4493df7e07e9eca47e
出典データセット
uspto-grants-2009_09
特許番号
US07585875B2

関連ノート

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