1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 137010778, compound

HRID 2206118Notes

Reaction equation

HRID 2206118 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][NH:13][C:12](=[O:17])[C:11]=3[C:10]([C:18]3[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[S:21][CH:22]=3)=[N:9]2)=[CH:5][CH:4]=1.[CH3:28]CN=C=NCCCN(C)C.Cl>CC(N(C)C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][NH:13][C:12](=[O:17])[C:11]=3[C:10]([C:18]3[CH:19]=[C:20]([C:23]([O:25][CH3:28])=[O:24])[S:21][CH:22]=3)=[N:9]2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 137010682HCID 137010682, compound

Product 1

HCID 137010778HCID 137010778, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(1-(4-methoxybenzyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acid (38.8 mg) in DMA (3 mL) were added EDCI hydrochloride (23.4 mg) and HOBt ammonium salt (18.6 mg) at room temperature, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. 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/methanol) to give the title compound (31.4 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/methanol)

Sources & evidence

ORD record
ord-51eb94cdf92442779a8ccec969fca289
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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