Ammonium → HCID 59258846, compound

HRID 641654Notes

Reaction equation

HRID 641654 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13](S(C)(=O)=O)[N:14]=[C:15]([CH3:16])[C:10]=3[CH:9]=[C:8]([C:21]3[CH:22]=[N:23][N:24]([CH2:26][CH2:27][O:28]COC)[CH:25]=3)[C:7]2=[O:32])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+:33]>O1CCOCC1.[Cl-].[Na+].O>[NH2:33][C:13]1[N:14]=[C:15]([CH3:16])[C:10]2[CH:9]=[C:8]([C:21]3[CH:22]=[N:23][N:24]([CH2:26][CH2:27][OH:28])[CH:25]=3)[C:7](=[O:32])[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 223AmmoniumHCID 59258908HCID 59258908, compound

Product 1

HCID 59258846HCID 59258846, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of 8-cyclopentyl-6-(1-(2-(methoxymethoxy)ethyl)-1H-pyrazol-4-yl)-4-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (80 mg, 0.17 mmol) in 5 ml 1,4-dioxane was babbled through ammonium gas for 10 minutes. The reaction tube was sealed and heated to 100° C. for 30 minutes. The reaction mixture was poured into brine and the precipitate was collected via filtration. The solid was then re-dissolved in 5 ml methanol and a few drop of concentrated HCl was added and the mixture was heated to 50° C. for 5 hours. The reaction mixture was cooled down to room temperature. Solvent was removed via rot vap and the residue was triturated with ethylacetate/hexane to give the title compound (33 mg, 54% yield).

Workup

  1. customThe reaction tube was sealed
  2. filtrationthe precipitate was collected via filtration
  3. dissolutionThe solid was then re-dissolved in 5 ml methanol
  4. additiona few drop of concentrated HCl was added
  5. temperaturethe mixture was heated to 50° C. for 5 hours
  6. temperatureThe reaction mixture was cooled down to room temperature
  7. customSolvent was removed via rot vap
  8. customthe residue was triturated with ethylacetate/hexane

Sources & evidence

ORD record
ord-a4c4c6345f524045b7ddee8980380e3e
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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