1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 72550085, compound

HRID 2205965Notes

Reaction equation

HRID 2205965 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[C:8]([C:16]3[CH:17]=[C:18]([C:21]([OH:23])=O)[S:19][CH:20]=3)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC[N:26]=C=NCCCN(C)C.Cl>CC(N(C)C)=O.O>[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=3[C:8]([C:16]3[CH:17]=[C:18]([C:21]([NH2:26])=[O:23])[S:19][CH:20]=3)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117988181HCID 117988181, compound

Product 1

HCID 72550085HCID 72550085, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)thiophene-2-carboxylic acid (62.5 mg) in DMA (2 mL) were added EDCI hydrochloride (43.8 mg) and HOBt ammonium salt (34.7 mg) at room temperature, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol) to give the title compound (55.9 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol)

Sources & evidence

ORD record
ord-6034733f11e34753b93312ad83b40ec3
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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