Hydrochloric Acid → 1-{2-[(3,5-Bis-trifluoromethyl-benzyl)-(2-fluoro-5-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yl}-piperidine-4-carboxylic acid

HRID 604021Notes

Reaction equation

HRID 604021 reaction equation
N1CCC(C(OC([C:12]2[CH:13]=[N:14][C:15]([N:18]([CH2:31][C:32]3[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=3)[CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[F:30])=[N:16][CH:17]=2)C)=O)CC1.[OH-].[Na+].Cl.[C:49]([O:52]CC)(=[O:51])[CH3:50]>C(O)C>[F:45][C:42]([F:43])([F:44])[C:34]1[CH:33]=[C:32]([CH:37]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:35]=1)[CH2:31][N:18]([CH2:19][C:20]1[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][C:21]=1[F:30])[C:15]1[N:16]=[CH:17][C:12]([N:18]2[CH2:31][CH2:32][CH:50]([C:49]([OH:52])=[O:51])[CH2:20][CH2:19]2)=[CH:13][N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 866267791-{2-[(3,5-Bis-trifluoromethyl-benzyl)-(2-fluoro-5-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yl}-ethyl piperidine-4-carboxylate

Product 1

HCID 866267801-{2-[(3,5-Bis-trifluoromethyl-benzyl)-(2-fluoro-5-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yl}-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-{2-[(3,5-Bis-trifluoromethyl-benzyl)-(2-fluoro-5-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yl}-ethyl piperidine-4-carboxylate (105 mg) is dissolved in ethanol (4 ml) and thereto is added a 1N-aqueous sodium hydroxide solution (2 ml), and the mixture is stirred at room temperature for 2 hours. To the reaction solution are added 1N-hydrochloric acid and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give 1-{2-[(3,5-bis-trifluoromethyl-benzyl)-(2-fluoro-5-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yl}-piperidine-4-carboxylic acid (81 mg). MS (m/z): 625 [M+H]+

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→9:1)

Sources & evidence

ORD record
ord-9e5b99343511494aa9c7599e6105e1c1
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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