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

HRID 1396510
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HRID 1396510 반응식
[CH2:1]([O:8][C:9]1[CH:13]=[C:12](C(OCC)=O)[N:11]([CH2:19][CH2:20][NH:21][C:22]([O:24]C(C)(C)C)=O)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1.O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]2[C:22](=[O:24])[NH:21][CH2:20][CH2:19][N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 2

HCID 10340Sodium CarbonateHCID 86706489ethyl 3-(benzyloxy)-1-{2-[(tert-butoxycarbonyl)amino]ethyl}-1H-pyrazole-5-carboxylate

생성물 1

HCID 727147872-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one수율 99%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매
HCID 31275
1,4-Dioxane
용매

실험 절차

Ethyl 3-(benzyloxy)-1-{2-[(tert-butoxycarbonyl)amino]ethyl}-1H-pyrazole-5-carboxylate (0.51 g, 1.31 mmol) was dissolved in a 4 M solution of HCl in 1,4-dioxane (6.53 mL). The mixture was stirred at room temperature for 1 hour and then made basic using a saturated solution of Na2CO3. The mixture was stirred at room temperature for 1 hour, diluted with water and 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 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (0.31 g, 99% yield) as a white solid. C13H13N3O2. 1H NMR (400 MHz, CDCl3) δ ppm 3.63-3.73 (m, 2H), 4.13 (dd, J=6.9, 5.4 Hz, 2H), 5.13 (s, 2H), 6.20 (s, 1H), 7.22 (br. s., 1H), 7.23-7.28 (m, 1H), 7.28-7.34 (m, 2H), 7.34-7.41 (m, 2H).

후처리

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionextracted 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 10/90)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

출처 및 근거

ORD 기록
ord-43a5880769934af29a68ff4ab455dc9d
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901125B2

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