Morpholine → HCID 11156013, compound

HRID 2105211Notes

Reaction equation

HRID 2105211 reaction equation
CC1C=CC(S(O[CH2:12][C:13]2[N:18]=[C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[C:24]3[O:28][N:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH:25]=3)[N:16]=[C:15]([NH:35][CH:36]3[CH:40]=[C:39]([CH3:41])[NH:38][N:37]3S(C3C=CC(C)=CC=3)(=O)=O)[CH:14]=2)(=O)=O)=CC=1.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>>[O:55]1[CH2:56][CH2:57][N:52]([CH2:12][C:13]2[N:18]=[C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH:20]3[C:24]3[O:28][N:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH:25]=3)[N:16]=[C:15]([NH:35][C:36]3[CH:40]=[C:39]([CH3:41])[NH:38][N:37]=3)[CH:14]=2)[CH2:53][CH2:54]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86610854HCID 86610854, compound

Product 1

HCID 11156013HCID 11156013, compoundYield 86.9%

Conditions

Temperature
60 °C

Procedure

A mixture of 6-[(4-methylphenylsulphonyloxy)methyl]-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-2-N-[4-methylphenylsulphonyl]-1H-pyrazol-3-ylamino)pyrimidine (Method 52) (214 mg, 0.295 mmol) and morpholine (5 ml, 83.2 mmol) was heated at reflux for 2 hours. The volatiles were removed by evaporation and the residue was dissolved in methanol (10 ml) and 10M aqueous sodium hydroxide solution (3 ml). The mixture was heated at 60° C. for 1 hour. The volatiles were removed by evaporation and the residue dissolved in water, extracted with dichloromethane. The extracts were combined and the solvent removed by evaporation. The residue was purified by chromatography on silica gel, eluting with dichloromethane (100%) and then diethylether (100%). The purified product was triturated with diethylether and collected by filtration to give the title compound (125 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe volatiles were removed by evaporation
  4. dissolutionthe residue was dissolved in methanol (10 ml)
  5. customThe volatiles were removed by evaporation
  6. dissolutionthe residue dissolved in water
  7. extractionextracted with dichloromethane
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with dichloromethane (100%)
  11. customThe purified product was triturated with diethylether
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a0b29654fe5b4a0da3edd25bb5494731
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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