Sodium Carbonate → HCID 57411799, compound

HRID 2046167Notes

Reaction equation

HRID 2046167 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 57411799HCID 57411799, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5d8b70ad3bfa4d5b92c352f2b4a919ce
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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