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Water → N-[2-(2-ethyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]acetamide

HRID 887815
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인쇄 미리보기

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HRID 887815 반응식
[NH2:1][CH2:2][CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([CH2:21][CH3:22])[C:15]=3C(OCC)=O)[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31].O>Cl.O1CCCC1>[CH2:21]([C:14]1[CH:15]=[C:9]2[C:8]3[CH:4]([CH2:3][CH2:2][NH:1][C:30](=[O:32])[CH3:31])[CH2:5][CH2:6][C:7]=3[CH:12]=[CH:11][N:10]2[N:13]=1)[CH3:22]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59145884ethyl 9-(2-aminoethyl)-2-ethyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

생성물 1

HCID 59145906N-[2-(2-ethyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]acetamide수율 86.2%

시약·촉매·용매 2

HCID 313
Hydrochloric Acid
용매
HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

A mixture of ethyl 9-(2-aminoethyl)-2-ethyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (81.0 mg, 0.269 mmol) in 12M hydrochloric acid (3 mL) was stirred at 100° C. for 3 days, and the mixture was concentrated under reduced pressure. To a mixture of the residue and triethylamine (375 μL, 2.69 mmol) in tetrahydrofuran (2.7 mL) was added acetic anhydride (76.3 μL, 0.807 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 min. Water (50 μL) was added, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) to give the title compound (62.9 mg, yield 85%).

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 15 min
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)

출처 및 근거

ORD 기록
ord-1aececc5591e4f4fb0411629c842401d
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08247429B2

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