Hydrazine hydrate (1:1) → HCID 77933884, compound

HRID 1878586Notes

Reaction equation

HRID 1878586 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)[CH:16]=[C:4]2[N:3]=1.O.[NH2:28][NH2:29]>O1CCOCC1.O>[CH3:15][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[CH:20]=[N:28][NH:29][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)[CH:16]=[C:4]2[N:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86659733HCID 86659733, compound

Product 1

HCID 77933884HCID 77933884, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

There was suspended, in 1,4-dioxane (2.0 mL), 6-(5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidin-2-yl)-quinoline (83 mg, 0.23 mM) prepared in the preceding step 1, then hydrazine monohydrate (110 μL, 2.3 mM) was added to the suspension and the mixture was stirred for 8 hours while refluxing the same with heating. After the stirring operation, the reaction liquid was concentrated, the concentrate thus obtained was diluted with water and then the mixture was extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate and the solvent was distilled off. The resulting solid was dried in vacuo, suspended in ethanol (2.0 mL), then acetic acid (6.5 μL, 0.11 mM) and metatolualdehyde (30 μL, 0.25 mM) were added to the suspension and the mixture was stirred at room temperature for 2 hours. The precipitated solid was recovered through filtration and then washed with diethyl ether to thus give the title compound (60 mg, overall yield of these two steps: 56%).

Workup

  1. temperaturewhile refluxing the same
  2. temperaturewith heating
  3. customAfter the stirring operation, the reaction liquid
  4. concentrationwas concentrated
  5. concentrationthe concentrate thus
  6. customobtained
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off
  10. customThe resulting solid was dried in vacuo
  11. additionacetic acid (6.5 μL, 0.11 mM) and metatolualdehyde (30 μL, 0.25 mM) were added to the suspension
  12. stirringthe mixture was stirred at room temperature for 2 hours
  13. filtrationThe precipitated solid was recovered through filtration
  14. washwashed with diethyl ether

Sources & evidence

ORD record
ord-441fbb8311174ad7870040eb2f79acb5
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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