Triethylamine → HCID 66751075, compound

HRID 534990Notes

Reaction equation

HRID 534990 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:21])[C:18](O)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:23]([O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[CH2:23]([O:30][C:31]1[CH:32]=[CH:33][C:34]([NH:35][C:18](=[O:19])[C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:16][CH2:15]2)=[O:21])=[CH:36][CH:37]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27238314-Benzyloxyaniline hydrochlorideHCID 667508542-[4-(2-Tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid

Product 1

HCID 66751075HCID 66751075, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid (Example 44, 2.5 g, 8.61 mmol), 4-(benzyloxy)aniline hydrochloride (2.06 g, 10.3 mmol), triethylamine (1.8 mL, 12.9 mmol), EDCI (1.6 g, 10.3 mmol) and HOBt (1.58 g, 10.3 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 to 65:35) to give the title compound (3.64 g, 90%) as a white amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 to 65:35)

Sources & evidence

ORD record
ord-794e7044d32f47069259a8be593acf44
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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