Benzenamine, 4-(4-morpholinyl)- → HCID 67388756, compound

HRID 905698Notes

Reaction equation

HRID 905698 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10](S(C)(=O)=O)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.Cl.O1CCOCC1.C(=O)(O)[O-].[Na+]>O.CN1C(=O)CCC1>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]([NH:31][C:30]3[CH:29]=[CH:28][C:27]([N:24]4[CH2:25][CH2:26][O:21][CH2:22][CH2:23]4)=[CH:33][CH:32]=3)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 23071569HCID 23071569, compound

Product 1

HCID 67388756HCID 67388756, compoundYield 13.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A 6 ml portion of NMP solution containing 303 mg of 4-cyclohexylamino-2-(methylsulfonyl)pyrimidine-5-carboxamide was mixed with 1.05 ml of 1 M n-tetrabutylammonium fluoride/THF solution, followed by stirring at 90° C. for 1 hour. Next, this was mixed with 200 mg of 4-morpholinoaniline and 2.77 ml of 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at 90° C. for 3 hours. The reaction mixture was cooled down to room temperature, diluted with water, mixed with saturated sodium bicarbonate aqueous solution and then extracted with ethyl acetate-THF mixed solution. The organic layer was washed with saturated brine, and then the solvent was evaporated and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol) to obtain 54 mg of 4-cyclohexylamino-2-[(4-morpholinophenyl)amino]pyrimidine-5-carboxamide as a pale brown solid.

Workup

  1. stirringby stirring at 90° C. for 3 hours
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. extractionextracted with ethyl acetate-THF mixed solution
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-7185c310b5f94f9eb8a61f2e0d7f5cd4
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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