1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 59540096, compound

HRID 923431Notes

Reaction equation

HRID 923431 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@H:7]([NH:14][CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C>N1C=CC=CC=1.CN(C)C=O.CCOC(C)=O>[O:19]=[C:18]1[CH2:17][CH2:16][CH2:15][N:14]1[C@H:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21]

Participants

6

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59540152HCID 59540152, compound

Product 1

HCID 59540096HCID 59540096, compoundYield 86.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of example 128B (307 mg, 1.05 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (602 mg, 3.14 mmol) in pyridine (5 mL) and dimethylformamide (5 mL) was stirred at ambient temperature for 16 hours. The mixture was diluted with EtOAc and washed with H2O and brine. The organic was dried (MgSO4), filtered and concentrated. Purification by chromatography (silica gel, 60% EtOAc in Hexanes) afforded 249 mg (86%) of the title compound. MS (ESI) m/z 276 (M+H)+.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by chromatography (silica gel, 60% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-079acf9597d143cda87aa14a66aa5da0
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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