Dichloromethane → N-(4-methoxyphenyl)-3-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)propanamide hydrochloride

HRID 1071076노트

반응식

HRID 1071076 반응식
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([NH:7][C:8](=[O:32])[CH2:9][CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][CH2:24][C:12]2=3)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:43]>>[ClH:43].[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([NH:7][C:8](=[O:32])[CH2:9][CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:12]2=3)=[CH:5][CH:4]=1

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396876tert-butyl 6-[3-(4-methoxyanilino)-3-oxopropyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

생성물 1

HCID 22396982N-(4-methoxyphenyl)-3-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)propanamide hydrochloride수율 84%

실험 절차

tert-butyl 6-[3-(4-methoxyanilino)-3-oxopropyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.110 g, 0.238 mmol) was disolved in CH2Cl2 (5 mL) and trifluoroacetic acid (2.0 mL, 2.96 g, 26.0 mmol, 109 equiv.) was added. The resulting solution was stirred at rt for 2.5 h. The reaction mixture was concentrated to dryness, and the residue was partitioned between EtOAc and 1N NaOH. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The crude product (0.0805 g) was combined with EtOAc (2 mL), and 1M HCl in Et2O (2 mL) and the salt was collected by filtration. The salt was dried under vacuum over P2O5. N-(4-methoxyphenyl)-3-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)propanamide hydrochloride (0.0796 g) was obtained in 84% yield. 1H NMR (300 MHz, CD3OD) δ 2.76, 3.13-3.17, 3.28-3.39, 3.74, 4.55, 6.82, 7.08, 7.18, 7.26, 7.44, 7.47; MS (ESI+) for C22H25N3O2 m/z 364.1 (M+H)+.

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was partitioned between EtOAc and 1N NaOH
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationthe salt was collected by filtration
  10. dry with materialThe salt was dried under vacuum over P2O5

출처 및 근거

ORD 기록
ord-d4c5f27e0c314ead85d8d2b9f35a448b
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903090B2

반응 노트

불러오는 중…