Triethylamine → 3-(Ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide

HRID 2363944Notes

Reaction equation

HRID 2363944 reaction equation
[CH2:1]([NH:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([OH:17])=O)[CH3:2].[Cl-].[NH4+].C([N:22](CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>O.CN(C=O)C>[CH2:1]([NH:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([NH2:22])=[O:17])[CH3:2]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667437393-(Ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acid

Product 1

HCID 667438263-(Ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxamideYield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acid (0.415 g, 1.67 mmol), ammonium chloride (0.893 g, 16.7 mmol), triethylamine (2.35 mL, 16.7 mmol) and DMF (10 mL) was stirred for 5 min. Then, 1-hydroxybenzotriazole (0.676 g, 5.00 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.956 g, 5.00 mmol) were added and stirring was continued for 3 days. The mixture was then poured into sat. aqueous sodium hydrogen carbonate (100 mL) and water (60 mL). Extraction with ethyl acetate-tetrahydrofuran (3:1, 2×100 mL), washing with sat. aqueous sodium hydrogen carbonate and brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave a yellow solid. This solid was triturated with dichloromethane, and the precipitate was collected by filtration to afford the title compound (0.258 g, 62%) as a yellow solid:

Workup

  1. stirringstirring
  2. waitwas continued for 3 days
  3. extractionExtraction with ethyl acetate-tetrahydrofuran (3:1, 2×100 mL)
  4. washwashing with sat. aqueous sodium hydrogen carbonate and brine
  5. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  6. customgave a yellow solid
  7. customThis solid was triturated with dichloromethane
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ba0e15f43e1743b2a92a50c4458ab216
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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