Triethylamine → HCID 18412513, compound

HRID 50382Notes

Reaction equation

HRID 50382 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:10]([OH:12])=O)[S:9][C:5]=2[N:4]=[C:3]1[CH2:13][O:14][CH3:15].S(Cl)(Cl)=O.[CH3:20][O:21][C:22]([CH2:24][CH2:25][NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23].C(N(CC)CC)C>C(Cl)Cl.O1CCCC1>[C:27]1([N:26]([CH2:25][CH2:24][C:22]([O:21][CH3:20])=[O:23])[C:10]([C:8]2[S:9][C:5]3[N:4]=[C:3]([CH2:13][O:14][CH3:15])[N:2]([CH3:1])[C:6]=3[CH:7]=2)=[O:12])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 89103N-Phenyl-beta-alanine methyl esterHCID 184123181H-Thieno[2,3-d]imidazole-5-carboxylic acid, 2-(methoxymethyl)-1-methyl-

Product 1

HCID 18412513HCID 18412513, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 0.50 g (2.2 mmol) of 1-methyl-2-methoxymethylthieno[2,3-d]imidazol-5-yl-carboxylic acid in 20 mL of methylene chloride was mixed with 2.0 mL (3.2 g, 27 mmol) of thionyl chloride and refluxed for 60 minutes, during which time the solid gradually dissolved. After distillation of the liquid components, the crude product was taken up twice more in methylene chloride. After the solvent had been eliminated once more, the crude acid chloride was taken up in 20 mL of tetrahydrofuran and added dropwise to a mixture of 0.42 g (2.3 mmol) of N-(2-methoxycarbonylethyl)aniline and 0.92 mL (6.6 mmol) of triethylamine in 30 mL of tetrahydrofuran. After 16 hours stirring at 50° C., the solvent was eliminated and the crude product obtained was purified by chromatography (silica gel; methylene chloride/ethanol=100:1). Yield: 0.66 g (77% of theory); Rf value: 0.47 (silica gel; methylene chloride/ethanol=19:1).

Workup

  1. temperaturerefluxed for 60 minutes, during which time the solid
  2. dissolutiongradually dissolved
  3. distillationAfter distillation of the liquid components

Sources & evidence

ORD record
ord-4a77aa06b19c4f5cb74a9aacae018436
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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