Hydrochloric Acid → HCID 67172511, compound

HRID 872529Notes

Reaction equation

HRID 872529 reaction equation
Cl.O1CCOCC1.[Cl:8][C:9]1[C:10]([C:26]#[N:27])=[N:11][CH:12]=[C:13]([C:15]2[N:19](C3CCCCO3)[N:18]=[CH:17][CH:16]=2)[CH:14]=1>C(O)C>[Cl:8][C:9]1[C:10]([C:26]#[N:27])=[N:11][CH:12]=[C:13]([C:15]2[NH:19][N:18]=[CH:17][CH:16]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67171582HCID 67171582, compound

Product 1

HCID 67172511HCID 67172511, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 M hydrogen chloride in dioxane (1.1 ml, 4.40 mmol) was added to a solution of 3-chloro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)picolinonitrile (1.1 g, 3.81 mmol) in absolute ethanol (15 ml) and stirred at RT for 3 h. Solvents were evaporated and water was added to the residue. The mixture was neutralised with saturated NaHCO3 and extracted with EtOAc. The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to give 0.796 g of the product. 1H-NMR (400 MHz; d6-DMSO): δ 7.10 (d, 1H), 7.92 (d, 1H), 8.58 (d, 1H), 9.17 (d, 1H), 13.4 (bs, 1H).

Workup

  1. customSolvents were evaporated
  2. additionwater was added to the residue
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0a76c13c8d5a4f55b1c4ab640462b513
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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