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

HRID 1825010노트

반응식

HRID 1825010 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d044e2670f9f4d1ca59628ff8d0f2d96
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045544B2

반응 노트

불러오는 중…