Triethylamine → HCID 66743788, compound

HRID 2363937Notes

Reaction equation

HRID 2363937 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7](O)=[O:8].[Cl-].[NH4+].Cl.C([N:21]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([NH2:21])=[O:8]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 60097591HCID 60097591, compound

Product 1

HCID 66743788HCID 66743788, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-(pyridin-4-yl)thiophene-3-carboxylic acid (2.20 g, 10 mmol), ammonium chloride (1.09 g, 20 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 30 mmol) and 1-hydroxybenzotriazole (1800 mg, 12 mmol) in DMF (100 mL) was added triethylamine (3.0 g, 30 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. After removal of the solvent, the residue was purified by column chromatography on silica gel (MeOH: DCM=1:19) to give the title compound (1100 mg, 50%) as a brown solid:

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by column chromatography on silica gel (MeOH: DCM=1:19)

Sources & evidence

ORD record
ord-3a39cee2396f4b3cb991e3d4bd1ff505
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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