Ethanol → HCID 76814766, compound

HRID 1878536Notes

Reaction equation

HRID 1878536 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]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:32][NH2:33].[CH2:34](O)[CH3:35]>>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[CH:16]=[C:4]3[N:3]=[C:2]([NH:32][N:33]=[CH:22][C:17]4[CH:15]=[CH:16][CH:4]=[C:34]([CH3:35])[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 86659714HCID 86659714, compound

Product 1

HCID 76814766HCID 76814766, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 5-chloro-2-(4-methoxy-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (64.8 mg, 0.188 mM) and then potassium carbonate (28.6 mg, 0.198 mM) and hydrazine monohydrate (91.2 μL, 1.88 mM) were added to the suspension. This suspension was stirred at 150° C. for 25 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, 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 (22.1 μL, 0.188 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 (54.6 mg, overall yield of these two steps: 66%).

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 (22.1 μL, 0.188 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-cd7c51d8db824d9596f7d61b42e101b7
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

Loading…