Triethylamine → HCID 140572978, compound

HRID 2370308Notes

Reaction equation

HRID 2370308 reaction equation
C(OC(=O)[C:5](=[N:7][O:8][CH2:9][CH2:10][CH3:11])[CH3:6])C.[OH-].[Na+].C(Cl)(=O)[C:16](Cl)=[O:17].C(N(CC)CC)C.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][O:36]/[N:37]=[C:38](\[C:45]2[N:49]([CH3:50])[N:48]=[N:47][N:46]=2)/[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:30]=1>CO.C(Cl)Cl>[CH2:9]([O:8][N:7]=[CH:5][CH2:6][C:16]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][O:36]/[N:37]=[C:38](\[C:45]2[N:49]([CH3:50])[N:48]=[N:47][N:46]=2)/[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:30]=1)=[O:17])[CH2:10][CH3:11]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 585674246‐({[(Z)‐[(1‐Methyl‐1H‐1,2,3,4‐tetrazol‐5‐ yl)(phenyl)methylidene]amino]oxy}methyl)pyridin‐2‐ amineHCID 76832219HCID 76832219, compound

Product 1

HCID 140572978HCID 140572978, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

0.12 g (0.70 mmol) of 2-n-propoxyimino-propionic acid ethyl ester was dissolved in 2 ml of methanol and 0.035 g (0.91 mmol) of sodium hydroxide was added to the resulting solution, followed by stirring for 1 hour at room temperature. The solvent was distilled off under reduced pressure, and neutralized with 2N hydrochloric acid, and extracted with chloroform. The organic layer was dried by adding magnesium sulfate, and concentrated tinder reduced pressure to obtain a white solid substance. The white solid substance was dissolved in 5 ml of methylene chloride, and stirred for 40 minutes at room temperature after adding 0.11 g (0.84 mmol) of oxalyl chloride, and concentrated tinder reduced pressure. The residue was dissolved in 5 ml of methylene chloride and stirred for 1 hour at room temperature after adding 0.10 g (0.99 mmol) of triethylamine and 0.14 g (0.45 mmol) of (Z)-(1-methyl-1H-tetrazol-5-yl)phenyl methanone-O-[2-aminopyridin-6-yl methyl]-oxime. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1 (v/v)) to obtain 0.10 g of the target compound.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. additionby adding magnesium sulfate
  5. concentrationconcentrated tinder reduced pressure
  6. customto obtain a white solid substance
  7. stirringstirred for 40 minutes at room temperature
  8. concentrationconcentrated tinder reduced pressure
  9. dissolutionThe residue was dissolved in 5 ml of methylene chloride
  10. stirringstirred for 1 hour at room temperature
  11. distillationThe solvent was distilled off
  12. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1 (v/v))

Sources & evidence

ORD record
ord-9c100a68cc064d919005989fdd9c9471
Source dataset
uspto-grants-2014_04
Patent number
US08710084B2

Reaction notes

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