Ethanol → HCID 76814765, compound

HRID 1878538Notes

Reaction equation

HRID 1878538 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:23]=[C:11]3[N:12]=[C:13](Cl)[CH:14]=[C:15]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:10]3[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:31][NH2:32].[CH2:33](O)[CH3:34]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:23]=[C:11]3[N:12]=[C:13]([NH:31][N:32]=[CH:8][C:5]4[CH:4]=[CH:3][CH:2]=[C:33]([CH3:34])[CH:6]=4)[CH:14]=[C:15]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 58531012HCID 58531012, compound

Product 1

HCID 76814765HCID 76814765, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 2-(4-bromo-phenyl)-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (59.3 mg, 0.179 mM) and then potassium carbonate (27.2 mg, 0.197 mM) and hydrazine monohydrate (86.8 μL, 1.79 mM) were added to the suspension. This suspension was stirred at 150° C. for 20 minutes under the irradiation with microwaves. 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, dried over anhydrous sodium sulfate and the solvent was then distilled off. The resulting residue was suspended in ethanol (2 mL), then acetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (21.1 μL, 0.179 mM) were added to the suspension and the mixture was stirred at room temperature for one hour. This reaction mixture was filtered and the resulting solid was purified by the NH-silica gel column chromatography (methylene chloride) to thus give the title compound (30.7 mg, overall yield of these two steps: 35%).

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 then distilled off
  7. additionacetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (21.1 μL, 0.179 mM) were added to the suspension
  8. stirringthe mixture was stirred at room temperature for one hour
  9. filtrationThis reaction mixture was filtered
  10. customthe resulting solid was purified by the NH-silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-fa5e4e153f4343b78fc4a3cdd6b00216
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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