Triethylamine → HCID 178468852, compound

HRID 43828Notes

Reaction equation

HRID 43828 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H: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])[CH2:4][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][C@H:2]2[CH2:7][CH2:6][C@H: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])[CH2:4][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 178468850HCID 178468850, compound

Product 1

HCID 178468852HCID 178468852, compoundYield 53%

Reagents, catalysts & solvents 3

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

Procedure

Ethyl trans-3-(4-aminocyclohexyl)benzoate obtained in Example (193a) (50 mg, 0.202 mmol) was dissolved in a mixed solution of N,N-dimethylacetamide/dichloromethane=1/1 (8 mL). 4-Chloro-5-ethyl-1H-imidazole-2-carboxylic acid (described in Example 1d, 71 mg, 0.404 mmol), 1-hydroxybenzotriazole (109 mg, 0.808 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (155 mg, 0.808 mmol) and triethylamine (112 μL, 0.808 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 43 mg of the title compound as a white solid (53%).

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-fd341fa4f4344c019d8c56afae4a1b7c
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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