Ethanol → HCID 76814748, compound

HRID 1878532Notes

Reaction equation

HRID 1878532 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:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:31][NH2:32].[CH2:33](O)[CH3:34]>>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[CH:16]=[C:4]3[N:3]=[C:2]([NH:31][N:32]=[CH:22][C:17]4[CH:15]=[CH:16][CH:4]=[C:33]([CH3:34])[CH:18]=4)[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:18][CH:19]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 58531010HCID 58531010, compound

Product 1

HCID 76814748HCID 76814748, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 5-chloro-2-(4-chloro-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (50.0 mg, 0.143 mM) and then potassium carbonate (21.7 mg, 0.157 mM) and hydrazine monohydrate (69.4 μL, 1.43 mM) were added to the suspension. This suspension was stirred at 150° C. for 20 minutes, while applying microwaves to the same. This reaction liquid was diluted with a saturated aqueous common salt solution and then extracted with ethyl acetate. The extracts thus obtained were combined together and then dried over anhydrous sodium sulfate and the solvent was distilled off. The resulting residue was suspended in ethanol (2 mL), then acetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (17.0 μL, 0.144 mM) were added to the suspension and the mixture was stirred at room temperature for one hour. This reaction liquid was filtered and the resulting solid was purified by the NH-silica gel column chromatography (methylene chloride) to give the title compound (36.8 mg, overall yield of these two steps: 58%).

Workup

  1. customThis reaction liquid
  2. additionwas diluted with a saturated aqueous common salt solution
  3. extractionextracted with ethyl acetate
  4. customThe extracts thus obtained
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. additionacetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (17.0 μL, 0.144 mM) were added to the suspension
  8. stirringthe mixture was stirred at room temperature for one hour
  9. customThis reaction liquid
  10. filtrationwas filtered
  11. customthe resulting solid was purified by the NH-silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-99ff8ac9c970440888a4daa74936f5f0
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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