Hydrochloric Acid → 6-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile monohydrochloride

HRID 522304Notes

Reaction equation

HRID 522304 reaction equation
[ClH:1].[CH2:2]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([C:19]3[N:27]=[C:26]([C:28]#[N:29])[N:25]=[C:24]4[C:20]=3[N:21]=[CH:22][N:23]4[CH3:30])=[CH:15][C:14]=2[C:31]([F:34])([F:33])[F:32])[CH2:6][CH2:5]1)[CH3:3]>CCOC(C)=O.CCO>[ClH:1].[CH2:2]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][O:12][C:13]2[N:18]=[CH:17][C:16]([C:19]3[N:27]=[C:26]([C:28]#[N:29])[N:25]=[C:24]4[C:20]=3[N:21]=[CH:22][N:23]4[CH3:30])=[CH:15][C:14]=2[C:31]([F:33])([F:32])[F:34])[CH2:6][CH2:5]1)[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 717616296-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile

Product 1

HCID 1178995926-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile monohydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A 4 M solution of hydrogen chloride in EtOAc (4.2 mL) was added dropwise to a suspension of 6-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile (3.9 g) in EtOH (58.5 mL) at room temperature, whereby a solution was obtained. After the solution was concentrated under reduced pressure, the residue was suspended in EtOH (117 mL). The suspension was stirred at 80° C. to obtain a solution, and the solution was cooled to room temperature while stirring. The solution was stirred at room temperature overnight. The precipitated solid was filtered, and the solid was washed with EtOH, whereby 6-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile monohydrochloride (3.2 g) was obtained as a crystal (heat absorption peak temperature obtained by a TG/DTA analysis: near 220° C.).

Workup

  1. customwhereby a solution was obtained
  2. concentrationAfter the solution was concentrated under reduced pressure
  3. customto obtain a solution
  4. temperaturethe solution was cooled to room temperature
  5. stirringwhile stirring
  6. stirringThe solution was stirred at room temperature overnight
  7. filtrationThe precipitated solid was filtered
  8. washthe solid was washed with EtOH

Sources & evidence

ORD record
ord-396c0dad0d3b4c239aa9998bf3acf0f1
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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