1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 19082084, compound

HRID 963300Notes

Reaction equation

HRID 963300 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.Cl.C(N=C=NCCCN(C)C)C.[NH2:34][C:35]1[CH:40]=[CH:39][N:38]=[C:37]([CH2:41][CH3:42])[C:36]=1[Cl:43]>ClCCl>[Cl:43][C:36]1[C:37]([CH2:41][CH3:42])=[N:38][CH:39]=[CH:40][C:35]=1[NH:34][C:17](=[O:19])[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:21])[F:20])=[CH:8][N:7]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117894634-Pyridinamine, 3-chloro-2-ethyl-HCID 19082076HCID 19082076, compound

Product 1

HCID 19082084HCID 19082084, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.97 g (10.0 mmol) of 4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetic acid was dissolved in 20 ml of dichloromethane, and the solution was cooled to a temperature of from -10° to 0° C. Then, 2.30 g (12.0 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added thereto, and the mixture was stirred at a temperature of from -10° to 0° C. 30 minutes later, 1.57 g (10.0 mmol) of 4-amino-3-chloro-2-ethylpyridine was added thereto, and the mixture was gradually returned to room temperature with stirring and further stirred for 16 hours at room temperature. Then, 10 ml of dichloromethane was added to the reaction solution. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, dichloromethane was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 1.14 g of the desired product as colorless cotton-like crystals (melting point: 124.5° to 125° C.).

Workup

  1. temperaturethe solution was cooled to a temperature of from -10° to 0° C
  2. customwas gradually returned to room temperature
  3. stirringwith stirring
  4. stirringfurther stirred for 16 hours at room temperature
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, dichloromethane was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1d991828418249eb9e52ebd3dd99c996
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

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