Triethylamine → N-[2-(3-cyanophenoxy)ethyl]-4-[(pyridine-4-yl)amino]benzamide

HRID 747690Notes

Reaction equation

HRID 747690 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Br.[NH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:54]=[C:55]([CH:58]=[CH:59][CH:60]=1)[C:56]#[N:57]>Cl.O>[C:56]([C:55]1[CH:54]=[C:53]([CH:60]=[CH:59][CH:58]=1)[O:52][CH2:51][CH2:50][NH:49][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH:18][CH:17]=1)#[N:57]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 177887733-(2-Aminoethoxy)benzonitrile hydrobromideHCID 68830990HCID 68830990, compound

Product 1

HCID 68832693N-[2-(3-cyanophenoxy)ethyl]-4-[(pyridine-4-yl)amino]benzamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

180 mg (0.743 mmol) of ethyl 4-[(pyridine-4-yl)amino]benzoate was dissolved in 5 ml of concentrated hydrochloric acid, and the solution was stirred at 70° C. for 15 hours. The solvent was evaporated, and the residue was dissolved in 5 ml of dichloromethane. 0.23 ml (1.64 mmol) of triethylamine, 156 mg (0.82 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 208 mg (0.82 mmol) of 1-hydroxybenzotriazole and 199 mg (0.82 mmol) of 3-(2-aminoethoxy)benzonitrile hydrobromide were added to the solution, and they were stirred for 16 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 5 ml of dichloromethane
  3. stirringwere stirred for 16 hours
  4. customThe reaction liquid
  5. extractionAfter the extraction with ethyl acetate
  6. washthe organic layer was successively washed with water, 1 N sodium hydroxide and saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-a2848d6062a4443e91d576b536c5acfe
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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