Hydrazine hydrate (1:1) → HCID 70867220, compound

HRID 1878576Notes

Reaction equation

HRID 1878576 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:21]=[C:20]([CH3:22])[O:19][N:18]=3)[CH:16]=[C:4]2[N:3]=1.O.[NH2:24][NH2:25]>O1CCOCC1>[CH3:22][C:20]1[O:19][N:18]=[C:17]([C:15]2[CH:16]=[C:4]3[N:3]=[C:2]([NH:24][NH2:25])[CH:7]=[C:6]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)[N:5]3[N:14]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86659728HCID 86659728, compound

Product 1

HCID 70867220HCID 70867220, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

There was suspended, in 1,4-dioxane (20 mL), 5-chloro-2-(5-methylisoxazol-3-yl)-7-morpholin-4-yl-pyrazolo[1,5-a]-pyrimidine (0.82 g, 2.6 mM) prepared in the foregoing step 1, then hydrazine monohydrate (1.3 mL, 26 mM) was added to the suspension and the suspension was stirred for 3 hours while refluxing the same with heating. After the stirring operation, the reaction liquid was concentrated, the concentrate was then diluted with water and extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate and the solvent was distilled off to thus give a crude product of the title compound (210 mg, yield: 26%). MS (ESI) m/z (M+H)+ 316.

Workup

  1. temperaturewhile refluxing the same
  2. temperaturewith heating
  3. customAfter the stirring operation, the reaction liquid
  4. concentrationwas concentrated
  5. additionthe concentrate was then diluted with water
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4788c17b0fb34193945b00cd72b88519
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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