Triethylamine → 5-[(Bicyclo[2.2.1]hept-2-ylacetyl)amino]-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

HRID 1825010Notes

Reaction equation

HRID 1825010 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])=[CH:5]2.C(N(CC)CC)C.[CH:35]12[CH2:41][CH:38]([CH2:39][CH2:40]1)[CH2:37][CH:36]2[CH2:42][C:43](Cl)=[O:44]>C1COCC1.Cl>[CH:35]12[CH2:41][CH:38]([CH2:39][CH2:40]1)[CH2:37][CH:36]2[CH2:42][C:43]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([C:19]([NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:20])=[CH:5]2)=[O:44]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 146225842-(Bicyclo(2.2.1)heptan-2-yl)acetyl chlorideHCID 221446705-Amino-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

Product 1

HCID 221446675-[(Bicyclo[2.2.1]hept-2-ylacetyl)amino]-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under argon, 78 mg (0.22 mmol) of 5-amino-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide (Example LI) are dissolved in 2 ml of THF, and 24.4 mg (0.24 mmol) of triethylamine are added. The solution is cooled to 0° C., and a solution of 37.9 mg (0.22 mmol) of bicyclo[2.2.1]hept-2-ylacetyl chloride in 0.2 ml of THF is added dropwise. The reaction mixture is stirred at RT for 2 h and then diluted with 1-molar hydrochloric acid and extracted repeatedly with ethyl acetate. The combined organic phases are washed twice with saturated sodium chloride solution and once with sodium bicarbonate solution, dried over sodium sulphate and filtered. The residue obtained after removal of the solvent under reduced pressure is purified chromatographically on silica gel (mobile phase: dichloromethane/ethyl acetate). 31.5 mg (29% of theory) of the product are obtained.

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. washThe combined organic phases are washed twice with saturated sodium chloride solution and once with sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customThe residue obtained
  6. customafter removal of the solvent under reduced pressure
  7. customis purified chromatographically on silica gel (mobile phase: dichloromethane/ethyl acetate)
  8. custom31.5 mg (29% of theory) of the product are obtained

Sources & evidence

ORD record
ord-d044e2670f9f4d1ca59628ff8d0f2d96
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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