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

HRID 2046167
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2046167
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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

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

Produkt 1

HCID 574117992-(phenoxymethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-oneAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5d8b70ad3bfa4d5b92c352f2b4a919ce
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592422B2

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