Triethylamine → Ethyl 3-{4-[(4-chloro-5-ethyl-1H-imidazole-2-carbonyl)amino]cyclohex-1-enyl)benzoate

HRID 1425298Notes

Reaction equation

HRID 1425298 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH2:3]1.[Cl:19][C:20]1[N:21]=[C:22]([C:27](O)=[O:28])[NH:23][C:24]=1[CH2:25][CH3:26].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C)C(=O)C.ClCCl.O.C(O)(C(F)(F)F)=O.C(OCC)(=O)C>[Cl:19][C:20]1[N:21]=[C:22]([C:27]([NH:1][CH:2]2[CH2:7][CH2:6][C:5]([C:8]3[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=3)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH2:3]2)=[O:28])[NH:23][C:24]=1[CH2:25][CH3:26]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 67549303Ethyl 3-(4-aminocyclohex-1-enyl)benzoate

Product 1

HCID 67549169Ethyl 3-{4-[(4-chloro-5-ethyl-1H-imidazole-2-carbonyl)amino]cyclohex-1-enyl)benzoateYield 76.2%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 22392675Trifluoroacetic acid waterSolventHCID 85741463dichloromethane N,N-dimethylacetamideSolvent

Procedure

Ethyl 3-(4-aminocyclohex-1-enyl)benzoate obtained in Example (951c) (120 mg, 0.49 mmol) was dissolved in a mixed solution of N,N-dimethylacetamide/dichloromethane=1/1 (10 mL). 4-Chloro-5-ethyl-1H-imidazole-2-carboxylic acid (described in Example 1d, 86 mg, 0.49 mmol), 1-hydroxybenzotriazole (100 mg, 0.735 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (141 mg, 0.735 mmol) and triethylamine (102 μL, 0.735 mmol) were added, and the mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, washed with brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1) to obtain 150 mg of the title compound as a white solid (76%).

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-b28ac18b1c2e44e0a50e0b99ffae8bc6
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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