Pyridine → N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-(2-methoxyethyl)-2-oxoimidazolidine-1-carboxamide

HRID 2278971Notes

Reaction equation

HRID 2278971 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:16])=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.[CH3:23][O:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][N:29]([C:32](Cl)=[O:33])[C:28]1=[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:16][C:32]([N:29]3[CH2:30][CH2:31][N:27]([CH2:26][CH2:25][O:24][CH3:23])[C:28]3=[O:35])=[O:33])=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 904029725-((2-Chloropyridin-4-yl)oxy)-6-methylpyridin-2-amineHCID 904260833-(2-Methoxyethyl)-2-oxoimidazolidine-1-carbonyl chloride

Product 1

HCID 90426033N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-(2-methoxyethyl)-2-oxoimidazolidine-1-carboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0° C. mixture of Example A7 (0.350 g, 1.485 mmol) and pyridine (0.251 mL, 3.12 mmol) in DCM (10 mL) was treated with a solution of Example B4 (0.368 g, 1.782 mmol) in DCM (5 mL) and stirred at RT overnight. The mixture was treated with satd. NaHCO3, extracted with DCM (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified twice via silica gel chromatography (MeOH/DCM) to afford N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-3-(2-methoxyethyl)-2-oxoimidazolidine-1-carboxamide (487 mg, 81%) as a yellow oil. MS (ESI) m/z: 406.1 (M+H+).

Workup

  1. additionThe mixture was treated with satd
  2. extractionNaHCO3, extracted with DCM (2×)
  3. dry with materialthe combined organics were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified twice via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-8d41c27843ee4017b144884889f5a7ae
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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