Ethanol → HCID 75216465, compound

HRID 1878530Notes

Reaction equation

HRID 1878530 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][CH:20]=[C:19]([Cl:23])[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:19]1[CH:18]=[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:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 58531107HCID 58531107, compound

Product 1

HCID 75216465HCID 75216465, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 5-chloro-2-(3-chloro-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (50.5 mg, 0.145 mM) and then potassium carbonate (22.0 mg, 0.160 mM) and hydrazine monohydrate (35.2 μL, 0.725 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 and dried over anhydrous sodium sulfate and then 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 (17.1 μL, 0.145 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 give the title compound (42.8 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 distilled off
  7. additionacetic acid (5.0 μL, 0.087 mM) and 3-methyl-benzaldehyde (17.1 μL, 0.145 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-bc15d277bc174e98bc7bef3f4c6ba6c7
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

Loading…