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Water → tert-butyl N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

HRID 1181885
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HRID 1181885 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[C:11]1[N:16]2[N:17]=[C:18]([S:28][CH3:29])[C:19]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:15]2[CH:14]=[CH:13][CH:12]=1.[H-].[Na+].Br[CH2:33][CH:34]1[CH2:36][CH2:35]1.O>CN(C)C=O.C(OCC)(=O)C>[CH:34]1([CH2:33][N:20]([C:19]2[C:18]([S:28][CH3:29])=[N:17][N:16]3[C:11]([C:4]4[C:5]([CH3:10])=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=4[O:2][CH3:1])=[CH:12][CH:13]=[CH:14][C:15]=23)[C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:36][CH2:35]1
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7

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HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 21984503tert-Butyl N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

생성물 1

HCID 21984731tert-butyl N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

After dissolving tert-butyl N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (400 mg) in N,N-dimethylformamide (5 mL), sodium hydride (60%, 58 mg) was added while cooling on ice, and then (bromomethyl)cyclopropane (111 μL) was added and the mixture was stirred for 1 hour at 40° C. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract was washed with brine. After drying the obtained organic layer over anhydrous magnesium sulfate and filtering it, the solvent was concentrated under reduced pressure to obtain crude tert-butyl N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate. This was dissolved in ethyl acetate (10 mL) without purification, a 4 N hydrochloric acid/ethyl acetate solution (20 mL) was added, and the mixture was stirred at 40° C. for 1 hour. The reaction mixture was neutralized with 5 N aqueous sodium hydroxide while cooling on ice, and then extraction was performed with ethyl acetate and the organic layer was washed with brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was distilled off under reduced pressure to obtain the title compound (368 mg) as a yellow oil.

후처리

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. washthe extract was washed with brine
  4. dry with materialAfter drying the obtained organic layer over anhydrous magnesium sulfate
  5. filtrationfiltering it
  6. concentrationthe solvent was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9c6b186b3b91459b8e4e8a684b1e6c3f
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07285666B2

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