Hydrochloric Acid → HCID 135867273, compound

HRID 2076826Notes

Reaction equation

HRID 2076826 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]([NH2:15])=[NH:14])[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+].C([O:21][C:22]([C:24]1[CH:29]=[CH:28][N:27]=[N:26][C:25]=1Cl)=O)C.C([O-])([O-])=O.[K+].[K+].Cl>CO.CN(C=O)C.O>[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]2[NH:15][C:22](=[O:21])[C:24]3[CH:29]=[CH:28][N:27]=[N:26][C:25]=3[N:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 10942334Sodium MethoxideHCID 14542887Ethyl 3-chloropyridazine-4-carboxylateHCID 67098848HCID 67098848, compound

Product 1

HCID 135867273HCID 135867273, compoundYield 3.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-[2-(3-Chloro-phenyl)-ethoxy]-acetamidine hydrochloride (240 mg, 0.964 mmol; described in example 6.2) was dissolved in MeOH (2 ml) and NaOMe (30% solution in MeOH, 179 μl, 0.964 mmol) was added dropwise at 0° C. The suspension was stirred at ambient temperature for 15 min and then evaporated. To the remaining residue were added a solution of crude 3-chloro-pyridazine-4-carboxylic acid ethyl ester (180 mg) in DMF (3 ml) and subsequently K2CO3 (267 mg, 1.929 mmol) and the mixture was heated to 100° C. for 18 h. Then water was added, the pH was adjusted to 3 by addition of 0.1 N HCl and the mixture was extracted three times with CH2Cl2 and one time with ethyl acetate. The combined organic extracts were washed three times with diluted HCl (pH 3), dried (Na2SO4) and evaporated. The remaining residue was triturated with Et2O and the brown solid was filtered off and further purified by column chromatography (silica gel, CH2Cl2/MeOH 95:5) to give the title compound (11 mg, 0.035 mmol; 3.6%) as brown solid. MS: m/e=317.1 [M+H+].

Workup

  1. customevaporated
  2. temperaturethe mixture was heated to 100° C. for 18 h
  3. extractionthe mixture was extracted three times with CH2Cl2 and one time with ethyl acetate
  4. washThe combined organic extracts were washed three times with diluted HCl (pH 3)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe remaining residue was triturated with Et2O
  8. filtrationthe brown solid was filtered off
  9. customfurther purified by column chromatography (silica gel, CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-2e2077d645d74e34899ec02bced00409
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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