Hydrazine hydrate (1:1) → HCID 178465304, compound

HRID 2112939Notes

Reaction equation

HRID 2112939 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)[N:8]2[N:7]=1)[CH3:2].CO[C:27](OC)([N:29](C)C)[CH3:28].O.[NH2:35]N>CC(N(C)C)=O.O>[NH:8]1[CH:13]=[CH:14][N:16]=[N:7]1.[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[NH:35][N:29]=[C:27]([CH3:28])[N:16]=3)[N:8]2[N:7]=1)=[O:24])[CH3:2]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 44571956HCID 44571956, compound

Product 1

HCID 178465304HCID 178465304, 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 AcOH and hydrazine hydrate (0.1 mL, 1.85 mmol) was added. The mixture was heated at 90° C. for 2 h. All solvent was then removed under high vacuum and the resulting slurry suspended in sat. NaHCO3 solution (50 mL). Crude 1-ethyl-3-[5-(5-methyl-2H-[1,2,4]triazol-3-yl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea triazole) was isolated by filtration and dried. Purification by silica gel chromatography (0.5% c.NH3 in 10% MeOH/CH2Cl2 as eluant) gave the desired product. HRMS (FAB+) calcd C17H17N9O (MH+) 364.1634, found 364.1632.

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 AcOH
  8. temperatureThe mixture was heated at 90° C. for 2 h
  9. customAll solvent was then removed under high vacuum

Sources & evidence

ORD record
ord-420a96e78793445f9d0d0b5e6220835d
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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