Sodium Hydroxide → HCID 25218113, compound

HRID 604196Notes

Reaction equation

HRID 604196 reaction equation
[F:1][C:2]([F:56])([F:55])[C:3]1[CH:4]=[C:5]([CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1)[CH2:6][N:7]([CH2:25][C:26]1[CH:31]=[C:30]([O:32][C:33]([F:36])([F:35])[F:34])[CH:29]=[CH:28][C:27]=1[C:37]1[CH:42]=[C:41]([CH:43]([CH3:45])[CH3:44])[CH:40]=[CH:39][C:38]=1[O:46][CH3:47])[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[CH:10][N:9]=1.Cl.O1CCOCC1.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:56][C:2]([F:1])([F:55])[C:3]1[CH:4]=[C:5]([CH:48]=[C:49]([C:51]([F:52])([F:53])[F:54])[CH:50]=1)[CH2:6][N:7]([CH2:25][C:26]1[CH:31]=[C:30]([O:32][C:33]([F:36])([F:35])[F:34])[CH:29]=[CH:28][C:27]=1[C:37]1[CH:42]=[C:41]([CH:43]([CH3:45])[CH3:44])[CH:40]=[CH:39][C:38]=1[O:46][CH3:47])[C:8]1[N:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 86626926HCID 86626926, compound

Product 1

HCID 25218113HCID 25218113, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To tert-butyl 4-{2-[(3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethoxy-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butyrate (57 mg) is added 4N-hydrogen chloride/dioxane solution (2 ml) and the mixture is stirred at room temperature overnight. To the reaction solution are added an aqueous saturated sodium hydroxide solution and chloroform, and the mixture is separated, dried over magnesium sulphate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→23:2) to give 4-{2-[(3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethoxy-biphenyl-2-ylmethyl)-amino]-pyrimidin-5-yloxy}-butanoic acid (46.6 mg). MS (m/z): 746 [M+H]+

Workup

  1. customthe mixture is separated
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→23:2)

Sources & evidence

ORD record
ord-7891f4fc168a47248813cc177e3c10f8
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…