1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86682823, compound

HRID 1428174Notes

Reaction equation

HRID 1428174 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:4][CH:3]=1.[CH3:19][C:20]1[O:24][C:23]([CH2:25][CH2:26][C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)=[N:22][N:21]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:31][C:30]2[CH:32]=[CH:33][C:27]([CH2:26][CH2:25][C:23]3[O:24][C:20]([CH3:19])=[N:21][N:22]=3)=[CH:28][CH:29]=2)=[O:18])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 82230217HCID 82230217, compoundHCID 86682820HCID 86682820, compound

Product 1

HCID 86682823HCID 86682823, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2E)-3-[4-(4-fluorophenyl)pyridin-3-yl]prop-2-enoic acid (730 mg), 4-[2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]aniline (640 mg), 1-hydroxy-1H-1,2,3-benzotriazole monohydrate (505 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (733 mg) and N,N-dimethylformamide (15 mL) was stirred at room temperature for 21 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), and the obtained solid was recrystallized from water-containing ethanol to give the title compound (941 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  6. customthe obtained solid was recrystallized from water-
  7. additioncontaining ethanol

Sources & evidence

ORD record
ord-53a4c4edce1b458f97edab2c098ba4a0
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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