Triethylamine → HCID 59596423, compound

HRID 2264944Notes

Reaction equation

HRID 2264944 reaction equation
CO[C:3]([C:5]1[N:6]=[N:7][C:8]([Cl:12])=[CH:9][C:10]=1Cl)=[O:4].Cl.[CH2:14]([O:16][C:17](=[O:21])[CH2:18][NH:19][CH3:20])[CH3:15].C(N(CC)CC)C>C(#N)C>[CH2:14]([O:16][C:17]([C:18]1[N:19]([CH3:20])[C:10]2[CH:9]=[C:8]([Cl:12])[N:7]=[N:6][C:5]=2[C:3]=1[OH:4])=[O:21])[CH3:15]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 17848322Methyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 59596423HCID 59596423, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4,6-dichloro-pyridazine-3-carboxylic acid methyl ester (2.9 g, 14 mmol) and sarcosine ethyl ester hydrochloride (2.15 g, 14 mmol) in acetonitrile (75 ml) was added triethylamine (4.9 mL, 35 mmol). The resultant reaction mixture was stirred at room temperature for 2 hours before adding further triethylamine (4.9 mL, 35 mmol) and heating the reaction mixture at 80° C. for 18 hours. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the resultant residue treated with water and extracted with ethyl acetate (×3), the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo to give a solid. The solid was triturated in hot methanol to give the title compound as a yellow solid (1.6 g, 45%). LCMS (method B): RT=2.64 min, M+H+=256.

Workup

  1. customThe resultant reaction mixture
  2. temperatureheating the reaction mixture at 80° C. for 18 hours
  3. temperatureAfter cooling to room temperature
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. additionthe resultant residue treated with water
  6. extractionextracted with ethyl acetate (×3)
  7. dry with materialthe combined organic extracts dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a solid
  11. customThe solid was triturated in hot methanol

Sources & evidence

ORD record
ord-ae9fcfada23547039131fb1bcb33a5ee
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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