Pyridine → HCID 136381716, compound

HRID 1821369Notes

Reaction equation

HRID 1821369 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2/[C:14](/[NH:17][OH:18])=[N:15]\[H])=[N:2]1.N1C=CC=CC=1.[CH2:29]([O:31]C(Cl)=O)C.CC(C)([O-])C.[K+].C(O)(=O)/C=C/C(O)=O>CN(C=O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[C:14]2[NH:15][C:29](=[O:31])[O:18][N:17]=2)=[N:2]1

Participants

8

Reactant 5

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 444972Fumaric AcidHCID 23665647Potassium tert-butoxideHCID 178506493HCID 178506493, compound

Product 1

HCID 136381716HCID 136381716, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(E)-2-[2-(1H-indazol-3-yl)vinyl]-N-hydroxybenzamidine (0.06 g, 0.22 mmol) obtained in Step 1 of Example 175 was dissolved in DMF (1.0 mL), and pyridine (35 μL, 0.43 mmol) and ethylchloroformate (0.12 mL, 1.1 mmol) were added thereto, followed by stirring at 0° C. for 30 minutes. The mixture was added with water and the precipitated solid was collected by filtration and the solid was dried. The obtained solid was dissolved in toluene (2.0 mL) at 0° C. and added with potassium tert-butoxide (85 mg, 0.76 mmol), followed by stirring at 60° C. for 2 hours. Then, the mixture was neutralized using aqueous fumaric acid solution. The reaction mixture was extracted with ethyl acetate and the organic layer was concentrated. The residue was triturated in a mixed solvent of ethyl acetate/hexane to obtain Compound 178 (18 mg, 23%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customthe solid was dried
  3. dissolutionThe obtained solid was dissolved in toluene (2.0 mL) at 0° C.
  4. stirringby stirring at 60° C. for 2 hours
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. concentrationthe organic layer was concentrated
  7. customThe residue was triturated in a mixed solvent of ethyl acetate/hexane

Sources & evidence

ORD record
ord-de46f0b83f3145bda4c1fad40fa72777
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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