1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86600615, compound

HRID 859853Notes

Reaction equation

HRID 859853 reaction equation
[CH2:1]([O:3][CH2:4][C:5](=[N:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[C:6]([OH:8])=O)[CH3:2].[NH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[N:27][CH:28]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[Cl:29][C:26]1[N:27]=[CH:28][C:23]([CH2:22][NH:21][C:6](=[O:8])[C:5](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:4][O:3][CH2:1][CH3:2])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 85847986HCID 85847986, compound

Product 1

HCID 86600615HCID 86600615, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3-ethoxy-2-(4-trifluoromethylphenyl hydrazono) propionic acid (0.3 g, 1 mmol), 5-aminomethyl-2-chloropyridine (0.21 g, 1.5 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloric acid salt (0.29 g, 1.5 mmol) and chloroform (10 ml) was left at room temperature overnight. The mixture was extracted with chloroform, washed 1N hydrochloric acid, a saturated sodium bicarbonate water and a saturated brine, dried on anhydrous sodium sulfate and then filtered. The residue obtained by concentrating the resulting filtrate was purified with a silica gel chromatography to obtain N-(6-chloro-3-pyridylmethyl)-3-ethoxy-2-(4-trifluoromethylphenyl hydrazono) propionic acid amide (Compound No. 170) (0.3 g, 0.72 mmol, 72%).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washwashed 1N hydrochloric acid
  3. dry with materiala saturated sodium bicarbonate water and a saturated brine, dried on anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe residue obtained
  6. concentrationby concentrating the resulting filtrate
  7. customwas purified with a silica gel chromatography

Sources & evidence

ORD record
ord-186a37ffcb044cf3b27d50c83406b6f7
Source dataset
uspto-grants-2006_12
Patent number
US07153815B2

Reaction notes

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