Hydrochloric Acid → 3-(2(1H)-pyridinon-5-yl)-2-phenylpyrazolo[1,5-a] pyrazine

HRID 1795862Notes

Reaction equation

HRID 1795862 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:11][N:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=23)=[CH:5][CH:4]=1.Cl.[OH-].[Na+]>O1CCOCC1>[NH:8]1[CH:7]=[C:6]([C:9]2[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:11][N:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=23)[CH:5]=[CH:4][C:3]1=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9922442HCID 9922442, compound

Product 1

HCID 99219923-(2(1H)-pyridinon-5-yl)-2-phenylpyrazolo[1,5-a] pyrazineYield 86.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(6-methoxy-3-pyridinyl)-2-phenylpyrazolo[1,5-a]pyrazine (2.36 g) and concd. HCl (7.8 mL) in 1,4-dioxane (48 mL) was stirred at 100° C. for 1 h. After cooling to room temperature, to the reaction mixture was added 5N sodium hydroxide solution and adjusted to pH 8, extracted with EtOAc, washed with brine, dried over sodium sulfate, evaporated in vacuo. The resulting solid was collected by filtration and washed with ether to give 3-(2(1H)-pyridinon-5-yl)-2-phenylpyrazolo[1,5-a]pyrazine (1.95 g) as a solid.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-926720594a284057a367ce0adde2759c
Source dataset
uspto-grants-2006_04
Patent number
US07030121B2

Reaction notes

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