Hydrochloric Acid → 4-{2-[(3,5-Bis-trifluoromethyl-phenyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyric acid

HRID 604152Notes

Reaction equation

HRID 604152 reaction equation
[F:1][C:2]([F:54])([F:53])[C:3]1[CH:4]=[C:5]([N:13]([CH2:31][C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:33]=2[C:42]2[CH:47]=[C:46]([CH:48]([CH3:50])[CH3:49])[CH:45]=[CH:44][C:43]=2[O:51][CH3:52])[C:14]2[N:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[CH:16][N:15]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl>O1CCOCC1.[Cl-].[Na+].O>[F:54][C:2]([F:1])([F:53])[C:3]1[CH:4]=[C:5]([N:13]([CH2:31][C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:35]=[CH:34][C:33]=2[C:42]2[CH:47]=[C:46]([CH:48]([CH3:50])[CH3:49])[CH:45]=[CH:44][C:43]=2[O:51][CH3:52])[C:14]2[N:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][N:19]=2)[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86626893Tert-butyl 4-{2-[(3,5-bis-trifluoromethyl-phenyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyrate

Product 1

HCID 866268944-{2-[(3,5-Bis-trifluoromethyl-phenyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyric acidYield 56.9%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To tert-butyl 4-{2-[(3,5-bis-trifluoromethyl-phenyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyrate (197 mg) is added a 4N-hydrochloric acid in dioxane (2.5 ml) and the mixture is stirred at room temperature for 3 hours. To the reaction mixture is added a saturated brine, and the mixture is extracted with ethyl acetate, 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→19:1) to give 4-{2-[(3,5-bis-trifluoromethyl-phenyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyric acid (104 mg). MS (m/z): 716 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  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→19:1)

Sources & evidence

ORD record
ord-55e650dc816243cca436b9c5234df193
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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