Triethylamine → HCID 57890442, compound

HRID 1820005Notes

Reaction equation

HRID 1820005 reaction equation
Cl.[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][CH:14]=1.ON1C2C=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=N1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.N1CCCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:20](=[O:22])[CH2:19][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][N:26]3[CH2:27][CH2:32][CH2:31][CH2:30]3)=[CH:18][CH:17]=2)=[CH:5][CH:4]=1

Participants

10

Reactant 7

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27240964-Bromobenzylamine hydrochlorideHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 57890442HCID 57890442, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-bromobenzylamine hydrochloride (971 mg, 4.37 mmol), [4-(bromomethyl)phenyl]acetic acid (1.00 g, 4.37 mmol), 1-hydroxybenzotriazole (590 mg, 4.37 mmol) and triethylamine (668 μl, 4.80 mmol) in dimethylformamide (11 ml) was added ethyldimethylaminopropylcarbodiimide hydrochloride (837 mg, 4.37 mmol) at 0° C., and the mixture was stirred at room temperature 16 hrs. Ethyl acetate was added to the reaction mixture. The mixture was washed with aqueous potassium carbonate solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate), and powderized with ethyl acetate-isopropyl ether (1:5). A solution of the obtained powder (850 mg, 2.24 mmol), pyrrolidine (561 μl, 6.37 mmol) and potassium carbonate (930 mg, 6.37 mmol) in dimethylformamide (10 ml) was stirred at 80° C. for 16 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate), and powderized with isopropyl ether to give the title compound (437 mg).

Workup

  1. washThe mixture was washed with aqueous potassium carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)
  5. washthe mixture was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-19cadf36458542d3a9eabbb12d583bc7
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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