1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 73062855, compound

HRID 859850Notes

Reaction equation

HRID 859850 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]=[C:11]([CH3:15])[C:12]([OH:14])=O)=[CH:5][CH:4]=1.[NH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[N:24][CH:25]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C=O>[Cl:26][C:23]1[N:24]=[CH:25][C:20]([CH2:19][NH:18][C:12](=[O:14])[C:11](=[N:10][NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:16])=[CH:8][CH:7]=2)[CH3:15])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 85847975HCID 85847975, compound

Product 1

HCID 73062855HCID 73062855, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-(4-Trifluoromethylphenyl hydrazono) propionic acid (12.31 g, 50.0 mmol) was dissolved in dichloromethane (250 ml) and N,N-dimethylformamide (25 ml), and 5-aminomethyl-2-chloropyridine (7.13 g, 50.0 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloric acid salt (9.59 g, 50.0 mmol) were added thereto. 30 hours later, the mixture was washed with 1N hydrochloric acid, a saturated sodium bicarbonate water and a saturated brine, and dried on sodium sulfate and then filtrated. The residue obtained by concentrating the resulting filtrate was purified with a silica gel chromatography to obtain N-(6-chloro-3-pyridylmethyl)-2-(4-trifluoromethylphenyl hydrazono) propionic acid amide (Compound No. 63) (14.47 g, 39.02 mmol, 78%).

Workup

  1. wash30 hours later, the mixture was washed with 1N hydrochloric acid
  2. dry with materiala saturated sodium bicarbonate water and a saturated brine, and dried on sodium sulfate
  3. filtrationfiltrated
  4. customThe residue obtained
  5. concentrationby concentrating the resulting filtrate
  6. customwas purified with a silica gel chromatography

Sources & evidence

ORD record
ord-4581bca7bda24713982617f52d4e48cd
Source dataset
uspto-grants-2006_12
Patent number
US07153815B2

Reaction notes

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