Sodium Carbonate → (2-(2-(5-((2'-fluorobiphenyl-4-yl)oxy)-2-pyridin-2-yl-1H-benzimidazol-6-yl)pyrrolidin-1-yl)-2-oxoethyl)methylamine

HRID 13402

Reaction equation

HRID 13402 reaction equation
C(O[C:6]([N:8](C)[CH2:9][C:10](O)=[O:11])=O)(C)(C)C.Cl.CN(C)CCCN=C=NCC.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2[C:54]([CH:55]3[CH2:59][CH2:58][CH2:57][NH:56]3)=[CH:53][C:43]3[NH:44][C:45]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=4)=[N:46][C:42]=3[CH:41]=2)=[CH:35][CH:34]=1.Cl.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:34]=[CH:35][C:36]([O:39][C:40]2[C:54]([CH:55]3[CH2:59][CH2:58][CH2:57][N:56]3[C:10](=[O:11])[CH2:9][NH:8][CH3:6])=[CH:53][C:43]3[NH:44][C:45]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=4)=[N:46][C:42]=3[CH:41]=2)=[CH:37][CH:38]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 204431481,4-Dioxane hydrochlorideHCID 231451105-((2'-fluorobiphenyl-4-yl)oxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole

Product 1

HCID 67482866(2-(2-(5-((2'-fluorobiphenyl-4-yl)oxy)-2-pyridin-2-yl-1H-benzimidazol-6-yl)pyrrolidin-1-yl)-2-oxoethyl)methylamine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

19 mg of N-(t-butoxycarbonyl)-N-methylglycine and 24 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added in order to a pyridin (1 ml) solution of 37 mg of 5-((2′-fluorobiphenyl-4-yl)oxy)-2-pyridin-2-yl-6-pyrrolidin-2-yl-1H-benzimidazole, and the reaction liquid was stirred at room temperature for 3 hours. 2 ml of 4 N hydrochloric acid-dioxane solution was added to the reaction liquid, and the reaction liquid was stirred at room temperature for 1 hour. The reaction liquid was diluted with chloroform, and made basic with aqueous saturated sodium carbonate added thereto, and the organic layer was washed with saturated saline and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=10/1) to obtain the entitled compound as a pale yellow solid.

Workup

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at room temperature for 1 hour
  4. customThe reaction liquid
  5. additionadded
  6. washthe organic layer was washed with saturated saline
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe solvent was evaporated away under reduced pressure
  9. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-f9da335b69ef4a00928c107b43ef988a
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

Loading…