Sodium Hydroxide → HCID 68837149, compound

HRID 2112940Notes

Reaction equation

HRID 2112940 reaction equation
[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:23]=[C:9]2[CH:10]=[C:11]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[C:13]([C:14]([NH2:16])=[O:15])[N:8]2[N:7]=1)[CH3:2].CO[C:27](OC)([N:29](C)C)[CH3:28].Cl.NO.[OH-].[Na+]>CC(N(C)C)=O.O>[CH2:1]([NH:3][C:4]([NH:5][C:6]1[N:23]=[C:9]2[CH:10]=[C:11]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[C:13]([C:14]3[O:15][N:29]=[C:27]([CH3:28])[N:16]=3)[N:8]2[N:7]=1)=[O:24])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 443297Hydroxyamine hydrochlorideHCID 44571956HCID 44571956, compound

Product 1

HCID 68837149HCID 68837149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid amide, which may be prepared as in Example 16, (200 mg, 0.62 mmol) was suspended in DMA (8 mL) and preheated to 90° C. Dimethylacetamide-dimethylacetal (0.45 mL, 3.07 mmol) was added and the solution was heated at 90° C. for 30 minutes. The reaction was allowed to cool, diluted with water (100 mL), then extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 fractions were washed with water (3×50 mL), brine (50 mL), and dried (Na2SO4). The mixture was filtered under reduced pressure. The resultant oil was dissolved in a mixture of dioxane and acetic acid (3 mL of a 1:1 mixture). Hydroxylamine hydrochloride (64 mg, 0.92 mmol) and 2 M NaOH solution (0.46 mL, 0.92 mmol) were added and the mixture was stirred at 90° C. for 2 h. The reaction mixture was allowed to cool, concentrated under reduced pressure and diluted with water (50 mL) to afford a precipitate. The precipitate was collected by filtration, then purified by chromatography on silica gel (5% MeOH/CH2Cl2 as eluant) to give the desired product, 1-ethyl-3-[5-(3-methyl-[1,2,4]oxadiazol-5-yl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea (27) as a solid mp. 298-301° C.

Workup

  1. custompreheated to 90° C
  2. temperatureto cool
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. washThe combined CH2Cl2 fractions were washed with water (3×50 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationThe mixture was filtered under reduced pressure
  7. dissolutionThe resultant oil was dissolved in a mixture of dioxane and acetic acid (3 mL of a 1:1 mixture)
  8. temperatureto cool
  9. concentrationconcentrated under reduced pressure
  10. additiondiluted with water (50 mL)
  11. customto afford a precipitate
  12. filtrationThe precipitate was collected by filtration
  13. custompurified by chromatography on silica gel (5% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-131e2cee186a4eab86db75f7fde04de0
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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