Pyridine → N-(5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide

HRID 2278968Notes

Reaction equation

HRID 2278968 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[O:22]=[C:23]1[N:27]([CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH2:26][CH2:25][N:24]1[C:34](Cl)=[O:35]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:34]([N:24]3[CH2:25][CH2:26][N:27]([CH:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[C:23]3=[O:22])=[O:35])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 593227885-(2-Chloropyridin-4-yloxy)pyridin-2-amineHCID 904274552-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carbonyl chloride

Product 1

HCID 90426999N-(5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamideYield 119%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0° C. mixture of Example A5 (1 g, 4.51 mmol) and pyridine (1.1 mL, 13.6 mmol) in DCM (25 mL) was treated with a solution of Example B2 (1.680 g, 7.22 mmol) in DCM (8 mL), warmed to RT and stirred 45 min. The mixture was concentrated to dryness, the residue treated with DCM and Et2O, sonicated and the resulting solid collected via filtration. The solid was dissolved in DCM, washed with water, the aqueous layer back-extracted with DCM (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford N-(5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (2.24 g, 119%) which was used without further purification. MS (ESI) m/z: 418.1 (M+H+).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additionthe residue treated with DCM and Et2O
  3. customsonicated
  4. filtrationthe resulting solid collected via filtration
  5. dissolutionThe solid was dissolved in DCM
  6. washwashed with water
  7. extractionthe aqueous layer back-extracted with DCM (3×)
  8. dry with materialthe combined organics were dried over Na2SO4
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-68a1197d3fa74e2394652ee60223f16e
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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