Triethylamine → HCID 66743384, compound

HRID 2363927Notes

Reaction equation

HRID 2363927 reaction equation
[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([OH:16])=O.[Cl-].[NH4+].C([N:21](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>[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([NH2:21])=[O:16]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66743147HCID 66743147, compound

Product 1

HCID 66743384HCID 66743384, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(methylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acid (0.342 g, 1.46 mmol), ammonium chloride (0.781 g, 14.6 mmol), triethylamine (2.05 mL, 14.6 mmol) and DMF (8.7 mL) was stirred for 5 min. Then, 1-hydroxybenzotriazole (0.592 g, 4.38 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.840 g, 4.38 mmol) were added and stirring was continued for 3 days. The mixture was poured into a mixture of 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 (0.219 g, 64%) 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-56d0be694e9e43778a6a4dcb8b5e8cc1
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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