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Sodium Carbonate → 2-(phenoxymethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

HRID 2046167
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HRID 2046167 반응식
C(OC([C:6]1[N:7]([CH2:19][CH2:20][NH:21][C:22]([O:24]C(C)(C)C)=O)[N:8]=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=1)=O)C.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1>[O:12]([CH2:11][C:9]1[CH:10]=[C:6]2[C:22](=[O:24])[NH:21][CH2:20][CH2:19][N:7]2[N:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 679582242-(2-tert-Butoxycarbonylamino-ethyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester

생성물 1

HCID 574117992-(phenoxymethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one수율 86.7%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

2-(2-tert-Butoxycarbonylamino-ethyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.72 g, 1.85 mmol) was dissolved in a 4M solution of HCl in 1,4-dioxane (7 mL) under N2. The mixture was stirred at room temperature for 1 hour. The mixture was basified with a saturated solution of Na2CO3 and stirred at room temperature for 72 hours. Then the mixture was extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 5/95). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (0.39 g, 85% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 3.71-3.86 (m, 2H), 4.32-4.48 (m, 2H), 5.11 (s, 2H), 6.39 (br. s., 1H), 6.91-6.99 (m, 2H), 7.00 (d, J=8.1 Hz, 2H), 7.27-7.34 (m, 2H).

후처리

  1. stirringstirred at room temperature for 72 hours
  2. extractionThen the mixture was extracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 5/95)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

출처 및 근거

ORD 기록
ord-5d8b70ad3bfa4d5b92c352f2b4a919ce
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08592422B2

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