Hydrochloric Acid → HCID 178464363, compound

HRID 604032Notes

Reaction equation

HRID 604032 reaction equation
[F:1][C:2]([F:53])([F:52])[C:3]1[CH:4]=[C:5]([CH:45]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:47]=1)[CH2:6][N:7]([CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[N:29]([CH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([CH2:39][C:40]([O:42]CC)=[O:41])[CH2:35][CH2:34]1)[CH2:30][CH3:31])[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][OH:17])=[CH:10][N:9]=1.[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C>[F:53][C:2]([F:1])([F:52])[C:3]1[CH:4]=[C:5]([CH:45]=[C:46]([C:48]([F:49])([F:50])[F:51])[CH:47]=1)[CH2:6][N:7]([CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[N:29]([CH2:32][C@H:33]1[CH2:34][CH2:35][C@H:36]([CH2:39][C:40]([OH:42])=[O:41])[CH2:37][CH2:38]1)[CH2:30][CH3:31])[C:8]1[N:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][OH:17])=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178471779HCID 178471779, compound

Product 1

HCID 178464363HCID 178464363, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl trans-[4-({[2-({(3,5-bis-trifluoromethyl-benzyl)-[5-(2-hydroxy-ethoxy)-pyrimidin-2-yl]-amino}-methyl)-4-trifluoromethyl-phenyl]-ethyl-amino}-methyl)-cyclohexyl]-acetate (122 mg) is dissolved in ethanol (4 ml), and thereto is added 1N-aqueous sodium hydroxide solution (1 ml) and the mixture is stirred at 60° C. for 2 hours. The reaction solution is cooled to room temperature, and thereto 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 (hexane:ethyl acetate=7:3→3:7) to give trans-[4-({[2-({(3,5-bis-trifluoromethyl-benzyl)-[5-(2-hydroxy-ethoxy)-pyrimidin-2-yl]-amino}-methyl)-4-trifluoromethyl-phenyl]-ethylamino}-methyl)-cyclohexyl]-acetic acid (50 mg). MS (m/z): 737 [M+H]+

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=7:3→3:7)

Sources & evidence

ORD record
ord-273e40cc398a4cbaa4b9f471604bac88
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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