Methylamine → HCID 59258825, compound

HRID 2389976Notes

Reaction equation

HRID 2389976 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.[CH3:33][NH2:34]>C1COCC1>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:34][CH3:33])[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][OH:28])[CH:25]=3)[C:7]2=[O:32])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59258908HCID 59258908, compound

Product 1

HCID 59258825HCID 59258825, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

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) was dissolved into 3 ml methylamine in THF (1.0 M). The reaction mixture was then heated to 100° C. in microwave for 30 minutes. The solvent was removed via rot vap and the residue was re-dissolved in 5 ml methanol. A few drop of concentrated HCl was added 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 (45 mg, 70% yield).

Workup

  1. customThe solvent was removed via rot vap
  2. dissolutionthe residue was re-dissolved in 5 ml methanol
  3. additionA few drop of concentrated HCl was added the mixture
  4. temperaturewas heated to 50° C. for 5 hours
  5. temperatureThe reaction mixture was cooled down to room temperature
  6. customSolvent was removed via rot vap
  7. customthe residue was triturated with ethylacetate/hexane

Sources & evidence

ORD record
ord-e9296f5cb013420c9b63d78c838516d9
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

Loading…