Hexahydro-1H-azepine-1-ethanamine → N-[2-(1-Azepanyl)ethyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide

HRID 1669034

반응식

HRID 1669034 반응식
[N:1]1([CH2:8][CH2:9][NH2:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:12]1[N:13]=[N+:14]([O-:25])[C:15]2[CH:24]=[C:23]3[C:19]([CH2:20][CH2:21][CH2:22]3)=[CH:18][C:16]=2[N:17]=1>COCCOC>[N:1]1([CH2:8][CH2:9][NH:10][C:12]2[N:13]=[N+:14]([O-:25])[C:15]3[CH:24]=[C:23]4[C:19]([CH2:20][CH2:21][CH2:22]4)=[CH:18][C:16]=3[N:17]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 40002Hexahydro-1H-azepine-1-ethanamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

생성물 1

HCID 67332497N-[2-(1-Azepanyl)ethyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide수율 56%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

2-(1-Azepanyl)ethylamine (289) (0.52 g, 3.6 mmol) was added to a stirred solution of chloride 21 (322 mg, 1.5 mmol) in DME (30 mL) and the solution stirred at reflux temperature for 3 h. The solvent was evaporated and the residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 46 (264 mg, 56%) as a yellow solid: mp (MeOH) 121-123° C.; 1H NMR δ 8.08 (s, 1H, H-9), 7.40 (s, 1H, H-5), 5.93 (br s, 1H, NH), 3.47-3.52 (m, 2H, CH2N), 2.97-3.03 (m, 4H, H-6, H-8), 2.74 (dd, J=6.0, 5.8 Hz, 2H, CH2N), 2.65-2.68 (m, 4H, 2×CH2N), 2.15 (p, J=7.4 Hz, 2H, H-7), 1.58-1.68 (m, 8H, 4×CH2); 13C NMR δ 158.8, 154.5, 148.8, 143.1, 129.7, 120.5, 114.6, 55.9, 55.1 (2), 38.8, 33.1, 32.3, 28.4 (2), 26.9 (2), 25.7. Anal. calcd for C18H25N5O: C, 66.0; H, 7.7; N, 21.4. Found: C, 66.0; H, 7.6; N, 21.5%.

후처리

  1. temperatureat reflux temperature for 3 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL)
  4. customThe organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with a gradient (0-10%) of MeOH/DCM

출처 및 근거

ORD 기록
ord-14f6fb15322a46e8be5341839b1fb49c
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

연결된 노트

불러오는 중…