Hydrochloric Acid → HCID 58748551, compound

HRID 1366291Notes

Reaction equation

HRID 1366291 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11](NC)=[O:12])[C:5]([Cl:19])=[CH:4][N:3]=1.Cl.Cl.[CH3:22][O:23][C:24]1[CH:30]=[C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:28]=[CH:27][C:25]=1[NH2:26].Cl.C([O-])(O)=[O:39].[Na+]>C(O)(=O)C>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([OH:12])=[O:39])=[N:7][C:2]([NH:26][C:25]2[CH:27]=[CH:28][C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:30][C:24]=2[O:23][CH3:22])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 116233102-Methoxy-4-morpholinoaniline dihydrochlorideHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide

Product 1

HCID 58748551HCID 58748551, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1.0 g (3.37 mmol) of 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide in 15 mL of acetic acid are added 2-methoxy-4-morpholinoaniline dihydrochloride (1.9 g, 6.73 mmol) and 6.0 mL of 1N ethanolic solution of hydrogen chloride (6.0 mmol). After the reaction mixture is stirred at 120° C. for 16 hours and cooled to room temperature, aqueous NaHCO3 solution is added to adjust the acidity between pH 5 and pH 6. The resulting precipitate is collected by a filtration and dried under reduced pressure to give 2-[5-chloro-2-(2-methoxy-4-morpholin-4-yl-phenyl-amino)-pyrimidin-4-ylamino]-benzoic acid (970 mg, 2.12 mmol, 63%) as ivory solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting precipitate is collected by a filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-615eb757181f4ca78004a37a02c66dcc
Source dataset
uspto-grants-2011_02
Patent number
US07893074B2

Reaction notes

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