Hydrochloric Acid → HCID 178525716, compound

HRID 1403150Notes

Reaction equation

HRID 1403150 reaction equation
[F:1][CH:2]([F:36])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH2:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([O:30]C)=[O:29])[CH2:24][CH2:23]3)[N:9]=2)[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=2[N:4]=1.[OH-].[Na+].Cl>CO.O1CCCC1>[F:36][CH:2]([F:1])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH2:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([OH:30])=[O:29])[CH2:24][CH2:23]3)[N:9]=2)[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=2[N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178501116HCID 178501116, compound

Product 1

HCID 178525716HCID 178525716, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl trans-4-[({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-yl}amino)methyl]cyclohexane carboxylate (150 mg) was dissolved in a mixed solvent of methanol (750 μL) and tetrahydrofuran (750 μL), and a 1 M aqueous sodium hydroxide solution (899 mL) was added thereto, followed by stirring at room temperature for 2 hours. After the completion of the reaction, 1 M hydrochloric acid was added thereto under ice-cooling until the reaction solution became weakly acidic, followed by stirring at 0° C. for 1 hour. The resulting solid was collected by filtration and washed with hexane to obtain trans-4-[({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-yl}amino)methyl]cyclohexanecarboxylic acid (74 mg) as a white powder.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling until the reaction solution
  3. stirringby stirring at 0° C. for 1 hour
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with hexane

Sources & evidence

ORD record
ord-b7599844f0c84a8c876dd7410ae446af
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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