1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 59331295, compound

HRID 1881954Notes

Reaction equation

HRID 1881954 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23]([OH:25])=O)=[C:20]([CH3:26])[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C[N:29](C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23]([NH2:29])=[O:25])=[C:20]([CH3:26])[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59331360HCID 59331360, compound

Product 1

HCID 59331295HCID 59331295, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (5 mL) of 5-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-3-methyl-1H-pyrrole-2-carboxylic acid (160 mg) in N,N-dimethylformamide were added under ice-cooling N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (125 mg) and 1-hydroxybenzotriazole-ammonia complex (100 mg). The reaction mixture was slowly warmed to room temperature, and stirred overnight. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (155 mg, yield 97%) was obtained as colorless amorphous crystals from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 375 (MH+).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1e6436a38cc0418b818672195d757ec4
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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