Diethylamine → HCID 10599908, compound

HRID 1288819Notes

Reaction equation

HRID 1288819 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:6]2=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:4]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[CH2:29]([NH:31][CH2:32][CH3:33])[CH3:30]>ClCCl>[CH2:29]([N:31]([CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:6]2=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:4]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:32][CH3:33])[CH3:30]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 10812046HCID 10812046, compound

Product 1

HCID 10599908HCID 10599908, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 6-chloromethyl-4-(3,4-dimethoxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate (1.5 g), diethylamine (1.04 g) and dichloromethane (35 ml) was stirred for 14 hours under reflux. The reaction mixture was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was subjected to column chromatography on silica gel. From the fraction eluted with chloroform, ethyl 6-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate (1.1 g, 68%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, m.p.110°-111° C.

Workup

  1. temperatureunder reflux
  2. washThe reaction mixture was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off
  5. washFrom the fraction eluted with chloroform

Sources & evidence

ORD record
ord-62b909b4f9a647ac8e1c0718ccaeed85
Source dataset
uspto-grants-1998_05
Patent number
US05747486

Reaction notes

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