Benzenamine, 4-(4-morpholinyl)- → HCID 9801356, compound

HRID 269830Notes

Reaction equation

HRID 269830 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1.[CH2:21]([NH:28][C:29]1[C:34]([C:35]([NH2:37])=[O:36])=[CH:33][N:32]=[C:31](Cl)[N:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN1C(=O)CCC1>[CH2:21]([NH:28][C:29]1[C:34]([C:35]([NH2:37])=[O:36])=[CH:33][N:32]=[C:31]([NH:11][C:10]2[CH:12]=[CH:13][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:8][CH:9]=2)[N:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 204431481,4-Dioxane hydrochlorideHCID 23071595HCID 23071595, compound

Product 1

HCID 9801356HCID 9801356, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A 5 ml NMP solution of 352 mg of 4-morpholinoaniline was mixed with 0.95 ml of 4 M hydrogen chloride/1,4-dioxane solution and 400 mg of 4-benzylamino-2-chloropyrimidine-5-carboxamide, followed by stirring at 90° C. for 3 hours. The reaction mixture was cooled down to room temperature, and then the precipitate was collected by filtration. The collected solid was mixed with saturated sodium bicarbonate aqueous solution and extracted with a mixed solution of THF-ethyl acetate. The organic layer was washed with saturated brine, and then the solvent was evaporated. The resulting residue was crystallized by adding methanol and then recrystallized (methanol-THF) to obtain 264 mg of 4-benzylamino-2-{[4-(morpholin-4-yl)phenyl]amino}pyrimidine -5-carboxamide as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. additionThe collected solid was mixed with saturated sodium bicarbonate aqueous solution
  4. extractionextracted with a mixed solution of THF-ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe resulting residue was crystallized
  8. additionby adding methanol
  9. customrecrystallized (methanol-THF)

Sources & evidence

ORD record
ord-438b5b502ac540c6a293975015c52011
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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