Triethylamine → 1-Methyl-2-methoxymethylthieno[2,3-d]imidazol-5-yl-carboxylic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A suspension of 0.50 g (2.2 mmol) of 1-methyl-2-methoxymethyl-thieno[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
- temperaturerefluxed for 60 minutes, during which time the solid
- dissolutiongradually dissolved
- distillationAfter distillation of the liquid components the crude product
Sources & evidence
- ORD record
- ord-de3c2335cfef46b1b70e98f6d9a05b58
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06087380
Reaction notes
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