Triethylamine → HCID 15870231, compound

HRID 2227622Notes

Reaction equation

HRID 2227622 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11](O)=[O:12])[CH:10]=[C:5]2[N:4]=[C:3]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.S(Cl)(Cl)=O.[CH2:28]([O:30][C:31]([CH2:33][CH2:34][NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:32])[CH3:29].C(N(CC)CC)C>ClCCl.O1CCCC1>[C:36]1([N:35]([CH2:34][CH2:33][C:31]([O:30][CH2:28][CH3:29])=[O:32])[C:11]([C:9]2[CH:10]=[C:5]3[N:4]=[C:3]([CH2:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=4)[N:2]([CH3:1])[C:6]3=[N:7][CH:8]=2)=[O:12])[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 10910393beta-Alanine, N-phenyl-, ethyl esterHCID 18412671HCID 18412671, compound

Product 1

HCID 15870231HCID 15870231, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.0 g (6.5 mmol) of 3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[4,5-b]pyridine-6-carboxylic acid in 100 ml dichloromethane was mixed with 20 ml thionyl chloride and refluxed for 2 hours. After the liquid components had been distilled. off, the crude product was taken up twice more in dichloromethane and the solvent was distilled off each time. The crude acid chloride thus obtained (2 g) was suspended in 100 ml of tetrahydrofuran and mixed with 1.2 g (6.5 mmol) of N-(2-ethoxycarbonylethyl)aniline. Then within 5 minutes 0.73 g (7.2 mmol) of triethylamine were added dropwise. After 1 hour's stirring, the solvent was distilled off in vacuo, the residue was taken up in ethyl acetate, the organic phase was washed with water and dried with sodium sulfate. After distillation of the solvent and flash chromatography (silica gel; dichloromethane to dichloromethane/ethanol=49:1), the desired compound was isolated as a brownish oil.

Workup

  1. temperaturerefluxed for 2 hours
  2. distillationAfter the liquid components had been distilled
  3. distillationthe solvent was distilled off each time
  4. customThe crude acid chloride thus obtained (2 g)
  5. distillationthe solvent was distilled off in vacuo
  6. washthe organic phase was washed with water
  7. dry with materialdried with sodium sulfate
  8. distillationAfter distillation of the solvent and flash chromatography (silica gel; dichloromethane to dichloromethane/ethanol=49:1)

Sources & evidence

ORD record
ord-c0f56d9302644519a30b8447ed9fb4b5
Source dataset
uspto-grants-2002_07
Patent number
US06414008B1

Reaction notes

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