1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86714709, compound

HRID 529223Notes

Reaction equation

HRID 529223 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]([C:18]2[S:22][C:21]([CH2:23][CH2:24][C:25]([OH:27])=O)=[C:20]([CH3:28])[CH:19]=2)=[O:17])=[CH:13][CH:12]=1)(=[NH:10])[NH2:9].CCN=C=N[CH2:36][CH2:37][CH2:38][N:39]([CH3:41])C.Cl>N1C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:38]([N:39]([C:25](=[O:27])[CH2:24][CH2:23][C:21]1[S:22][C:18]([C:16]([O:15][C:14]2[CH:13]=[CH:12][C:11]([C:8](=[NH:10])[NH2:9])=[CH:30][CH:29]=2)=[O:17])=[CH:19][C:20]=1[CH3:28])[CH2:41][C:3]([OH:5])=[O:4])[CH:37]=[CH2:36]

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86714711HCID 86714711, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 86714709HCID 86714709, compoundYield 242.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound (100 mg, 0.224 mmol) obtained in step 1, M-5 (49.9 mg, 0.291 mmol), and WSC hydrochloride (64.4 mg, 0.336 mmol) were dissolved in pyridine (0.5 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (1.0 ml) was added to the obtained residue, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by high performance liquid chromatography (water-acetonitrile, each containing 0.1% trifluoroacetic acid) to give the title compound (98.5 mg, 0.181 mmol, 81%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (1.0 ml)
  2. additionwas added to the obtained residue
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe obtained residue was purified by high performance liquid chromatography (water-acetonitrile

Sources & evidence

ORD record
ord-05374e04d27e448295db19f8f3335dd8
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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