Triethylamine → HCID 178433008, compound

HRID 534996Notes

Reaction equation

HRID 534996 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[CH3:19][C:20]1[NH:21][CH:22]=[C:23]([C:25](O)=[O:26])[N:24]=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>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:25]([C:23]2[N:24]=[C:20]([CH3:19])[NH:21][CH:22]=2)=[O:26])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochlorideHCID 178433052HCID 178433052, compound

Product 1

HCID 178433008HCID 178433008, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride (Reference Example 1, 1.63 g, 5.60 mmol), 2-methyl-1H-imidazole-4-carboxylic acid (1.0 g, 6.16 mmol), triethylamine (3.12 mL, 22.4 mmol), EDCI (0.96 g, 6.16 mmol) and HOBt (0.94 g, 6.16 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 16 h. To the reaction mixture was added saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution, 1 M HCl 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 98:2 to 75:25) to give the title compound (1.63 g, 89%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated NaHCO3 solution, 1 M HCl 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 98:2 to 75:25)

Sources & evidence

ORD record
ord-66c539f53c984cad979a23024b83efa4
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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