Hydrochloric Acid → 1-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime

HRID 731695

반응식

HRID 731695 반응식
[CH:1]([C:4]1[C:12]([C:13](=O)[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].Cl.[NH2:19][OH:20].[OH-].[Na+].Cl>CCO.O>[CH:1]([C:4]1[C:12]([C:13](=[N:19][OH:20])[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

7

반응물 4

HCID 313Hydrochloric AcidHCID 3671IbudilastHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

생성물 1

HCID 578374801-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime수율 74.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of 2.3 g (10 mmol) of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one in 32 ml of anhydrous EtOH was added hydroxylamine hydrochloride 1.5 g (20 mmol), followed by dropwise addition of 2.4 g NaOH in 6 ml of water. The mixture was stirred and refluxed over night. After cooling, the solution was poured into a solution of 8.3 ml of 6N HCl and 380 ml ice water with stirring for 30 minutes. The precipitate was filtered and washed with ethyl ether-hexane to furnish 1.2 g (74.5%) of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime (as a mixture of cis- and trans-isomers), which was separated on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant to yield 0.3 g (cis-) and 0.325 g (trans-) isomers of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime. Compound 1012.

후처리

  1. temperaturerefluxed over night
  2. temperatureAfter cooling
  3. stirringwith stirring for 30 minutes
  4. filtrationThe precipitate was filtered
  5. washwashed with ethyl ether-hexane

출처 및 근거

ORD 기록
ord-1e8d8006adb84642ac67f87e9cee1621
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585875B2

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