4-Methoxybenzoic Acid → HCID 58465615, compound

HRID 1842467Notes

Reaction equation

HRID 1842467 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.CN(C)C(F)=[N+](C)C.[N:34]1[N:38]2[CH2:39][CH2:40][NH:41][CH2:42][C:37]2=[CH:36][C:35]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44]>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:41]2[CH2:40][CH2:39][N:38]3[N:34]=[C:35]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:36]=[C:37]3[CH2:42]2)=[O:9])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 74784-Methoxybenzoic AcidHCID 8471TriethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 45934303Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Product 1

HCID 58465615HCID 58465615, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxybenzoic acid (0.187 g, 1.23 mmol) dissolved in N,N-dimethylformamide (5 mL) and triethylamine (0.428 mL, 3.07 mmol) was added tetramethylfluoroformamidinium hexafluorophosphate (0.406 g, 1.54 mmol) and the reaction mixture was stirred for 15 minutes. Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (0.2 g, 1.02 mmol) was added and the reaction continued to stir at room temperature for 5 hours. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified via silica gel chromatography (0-90% EtOAc/hexane) to afford ethyl 5-(4-methoxybenzoyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate Intermediate 27 (0.359 g, 100%). LC-MS: (FA) ES+330.

Workup

  1. stirringto stir at room temperature for 5 hours
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via silica gel chromatography (0-90% EtOAc/hexane)

Sources & evidence

ORD record
ord-eb13b4d12ccc4863b58b28d5270d05ad
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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