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

HRID 2363922Notes

Reaction equation

HRID 2363922 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([OH:15])=O.[Cl-].[NH4+].C([N:20](CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:20])=[O:15]

Participants

8

Reactant 6

HCID 8471Triethylamine2×HCID 25517Ammonium Chloride2×HCID 757711-Hydroxybenzotriazole2×HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 130923543-Amino-5-(pyridin-4-yl)thiophene-2-carboxylic acid

Product 1

HCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamideYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxylic acid (0.220 g, 1.00 mmol), ammonium chloride (0.267 g, 5.00 mmol), triethylamine (0.70 mL, 5.0 mmol) and DMF (3.0 mL) was stirred for 5 min. 1-Hydroxybenzotriazole (0.204 g, 1.50 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.286 g, 1.50 mmol) were added and stirring was continued overnight. Then, DMF (2 mL), ammonium chloride (0.267 g, 5.00 mmol), triethylamine (0.70 mL, 5.0 mmol), 1-hydroxybenzotriazole (0.204 g, 1.50 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.286 g, 1.50 mmol) were added again. After 6 h, the mixture was poured into aqueous sodium hydrogen carbonate (50 mL). Extraction with ethyl acetate-tetrahydrofuran (2:1, 2×30 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave the title compound (0.185 g, 84%) as a yellow solid:

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. waitAfter 6 h
  4. extractionExtraction with ethyl acetate-tetrahydrofuran (2:1, 2×30 mL)
  5. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure

Sources & evidence

ORD record
ord-f8cf7d4a50044255bf00cfb3e93e3915
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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