Ibudilast → Ibudilast

HRID 731694

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HRID 731694 반응식
[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]

참가 물질

9

반응물 4

HCID 3671IbudilastHCID 11430Potassium Carbonate3회HCID 14798Sodium HydroxideHCID 122915071-Amino-2-methylpyridinium Iodide

생성물 2

HCID 3671Ibudilast수율 51.3%HCID 113786582-Isopropylpyrazolo[1,5-a]pyridine수율 32.9%

시약·촉매·용매 3

HCID 962Water용매2회HCID 7346Isobutyric anhydride용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fc5801f80e854c4493df7e07e9eca47e
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585875B2

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