Hydrochloric Acid → HCID 59293394, compound

HRID 2387504Notes

Reaction equation

HRID 2387504 reaction equation
[CH3:1][O:2][CH:3]([O:29]C)[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][C:15]3=[O:28])=[CH:11][CH:12]=2)[CH:7]=[N:6]1.Cl.O>C1COCC1>[OH:29][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][C:15]3=[O:28])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59293407HCID 59293407, compound

Product 1

HCID 59293394HCID 59293394, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yl)-4-phenethylpyridin-2(1H)-one (1.77 g, 4.39 mmol) in THF (20 mL) was treated with aqueous HCl (20 mL, 2.0 M). The solution was heated at 60° for 18 h, allowed to cool and then treated with H2O (50 mL). The mixture was extracted with EtOAc (3×100 mL), dried with Na2SO4, filtered and concentrated to give the title compound (1.72 g, 98%) as an orange solid: ESI MS m/z 390 [M+H]+.

Workup

  1. temperatureThe solution was heated at 60° for 18 h
  2. temperatureto cool
  3. extractionThe mixture was extracted with EtOAc (3×100 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22950cefdbf14235920d1cf54c6975a5
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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