Triethylamine → HCID 66743627, compound

HRID 2363949Notes

Reaction equation

HRID 2363949 reaction equation
[CH2:1]([NH:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[S:7][C:6]=1[C:16]([OH:18])=O)[CH2:2][CH3:3].[Cl-].[NH4+].C([N:23](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:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[S:7][C:6]=1[C:16]([NH2:23])=[O:18])[CH2:2][CH3:3]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66742996HCID 66742996, compound

Product 1

HCID 66743627HCID 66743627, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(propylamino)-5-(pyridin-4-yl)thiophene-2-carboxylic acid (0.477 g, 1.82 mmol), ammonium chloride (0.974 g, 18.2 mmol), triethylamine (2.56 mL, 18.2 mmol) and DMF (11 mL) was stirred for 5 min. Then, 1-hydroxybenzotriazole (0.743 g, 5.50 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.05 g, 5.50 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 (0.374 g, 79%) 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-3795397a9be54e5c9836198a88b98da4
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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