Ethanol → HCID 75216494, compound

HRID 1878545Notes

Reaction equation

HRID 1878545 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]([NH:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:35][NH2:36].[CH2:37](O)[CH3:38]>>[CH3:27][O:26][CH2:25][CH2:24][NH:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[CH:16]=[C:4]3[N:3]=[C:2]([NH:35][N:36]=[CH:22][C:17]4[CH:15]=[CH:16][CH:4]=[C:37]([CH3:38])[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 86659715HCID 86659715, compound

Product 1

HCID 75216494HCID 75216494, compound

Conditions

Temperature
150 °C

Procedure

There was suspended, in ethanol (2 mL), 5-chloro-2-{4-(2-methoxy-ethyl-amino)-phenyl}-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (32.6 mg, 0.0841 mM) and then potassium carbonate (12.8 mg, 0.0925 mM) and hydrazine monohydrate (40.8 μL, 0.841 mM) were added to the suspension. This suspension was stirred at 150° C. for 30 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 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 (9.9 μL, 0.0841 mM) were added to the suspension and then the mixture was stirred at room temperature for 30 minutes. This reaction mixture was filtered and the resulting solid was purified by the NH-silica gel column chromatography (methylene chloride) and further the resulting solid was washed with methanol to thus give the title compound (10.6 mg, overall yield of these two steps: 26%).

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 (9.9 μL, 0.0841 mM) were added to the suspension
  8. stirringthe mixture was stirred at room temperature for 30 minutes
  9. filtrationThis reaction mixture was filtered
  10. customthe resulting solid was purified by the NH-silica gel column chromatography (methylene chloride)
  11. washfurther the resulting solid was washed with methanol

Sources & evidence

ORD record
ord-9965579f8ee54487a5b5671602bde0e8
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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