Sodium Hydroxide → HCID 67388656, compound

HRID 269833Notes

Reaction equation

HRID 269833 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:6][C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([O:25]CC)=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[N:8][CH:9]=1)=[O:3].[OH-].[Na+]>C1COCC1.CO>[NH2:1][C:2]([C:4]1[C:5]([NH:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[N:6][C:7]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]3)=[CH:15][CH:16]=2)=[N:8][CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 23071603HCID 23071603, compound

Product 1

HCID 67388656HCID 67388656, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 15 ml THF-methanol (1:1) solution of 750 mg of ethyl 1-(4-{[5-(aminocarbonyl)-4-(benzylamino)pyrimidin-2-yl]amino}phenyl)piperidine-4-carboxylate was mixed with 1 M sodium hydroxide aqueous solution, followed by stirring under heating at 60° C. for 1 hour. The reaction mixture was cooled down to room temperature and mixed with 1 M sodium hydroxide aqueous solution, and the precipitated solid was collected by filtration and washed with water and methanol. By recrystallizing the resulting solid from a THF-methanol mixed solvent, 361 mg of 1-(4-{[5-(aminocarbonyl)-4-(benzylamino)pyrimidin-2-yl]amino}phenyl)piperidine-4-carboxylic acid was obtained as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water and methanol
  4. customBy recrystallizing the resulting solid from a THF-methanol mixed solvent

Sources & evidence

ORD record
ord-08fe5b294aa04e7e99b34cf0879f4d24
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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