2-Hydrazinopyridine → HCID 136082873, compound

HRID 476213Notes

Reaction equation

HRID 476213 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[OH:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](=O)[CH2:19][C:20]#[N:21])=[CH:12][C:11]=1[O:23][CH3:24]>C(O)(=O)C>[NH2:21][C:20]1[N:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[N:2]=[C:18](/[CH:17]=[CH:16]/[C:13]2[CH:14]=[CH:15][C:10]([OH:9])=[C:11]([O:23][CH3:24])[CH:12]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 70663854HCID 70663854, compound

Product 1

HCID 136082873HCID 136082873, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

2-hydrazinopyridine (62 mg, 0.57 mmol) was added to a solution of Compound 10 (113 mg, 0.520 mmol) synthesized in Step 1 of Example D in acetic acid (3 mL), followed by stirring under reflux at 120° C. for 30 minutes. The reaction solution was concentrated by distillation under reduced pressure, and ethyl acetate (5 mL) and water (5 mL) were added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then separated by column chromatography (n-Hex/EtOAc=3/1 (v/v)) to afford the title compound.

Workup

  1. concentrationThe reaction solution was concentrated by distillation under reduced pressure, and ethyl acetate (5 mL) and water (5 mL)
  2. additionwere added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customseparated by column chromatography (n-Hex/EtOAc=3/1 (v/v))

Sources & evidence

ORD record
ord-50f52602884149f29cf674d7be893fbe
Source dataset
uspto-grants-2014_01
Patent number
US08637674B2

Reaction notes

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