Hydrochloric Acid → HCID 59614389, compound

HRID 409446Notes

Reaction equation

HRID 409446 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([N:18]3[CH2:22][C@@H:21]([N:23]([CH2:37][C:38]4[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:39]=4)[C:24]4[N:29]=[CH:28][C:27]([N:30]5[CH2:34][CH2:33][N:32]([CH3:35])[C:31]5=[O:36])=[CH:26][N:25]=4)[CH2:20][C@H:19]3[CH2:52][CH3:53])[C:15]([Cl:54])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>CCO>[F:47][C:44]([F:45])([F:46])[C:42]1[CH:43]=[C:38]([CH:39]=[C:40]([C:48]([F:49])([F:50])[F:51])[CH:41]=1)[CH2:37][N:23]([C:24]1[N:25]=[CH:26][C:27]([N:30]2[CH2:34][CH2:33][N:32]([CH3:35])[C:31]2=[O:36])=[CH:28][N:29]=1)[C@@H:21]1[CH2:22][N:18]([C:16]2[C:15]([Cl:54])=[CH:14][N:13]=[C:12]([N:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)[N:17]=2)[C@H:19]([CH2:52][CH3:53])[CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59614390HCID 59614390, compound

Product 1

HCID 59614389HCID 59614389, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-[4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(3-methyl-2-oxo-imidazolidin-1-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-chloro-pyrimidin-2-yl]-piperidine-4-carboxylic acid ethyl ester (70 mg, 0.09 mmol) in EtOH (1 mL) is added 1N NaOH (0.45 mL, 0.45 mmol). The reaction mixture is stirred at room temperature for 1 hour. After quench with 1N HCl (0.45 mL, 0.45 mmol), the mixture is washed with brine and extracted with EtOAc. The combined organic layer is dried over MgSO4 then concentrated under reduced pressure to give 1-[4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(3-methyl-2-oxo-imidazolidin-1-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-chloro-pyrimidin-2-yl]-piperidine-4-carboxylic acid (66 mg, 97%).

Workup

  1. washthe mixture is washed with brine
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer is dried over MgSO4
  4. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-63437980f7a2453cae738b8a83c48711
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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