(2-Aminoethyl)dipropylamine → N1-(1-Oxido-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine

HRID 1669003노트

반응식

HRID 1669003 반응식
[CH2:1]([N:4]([CH2:8][CH2:9][CH3:10])[CH2:5][CH2:6][NH2:7])[CH2:2][CH3:3].Cl[C:12]1[N:13]=[N+:14]([O-:25])[C:15]2[C:24]3[CH2:23][CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][C:16]=2[N:17]=1>COCCOC>[O-:25][N+:14]1[C:15]2[C:24]3[CH2:23][CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][C:16]=2[N:17]=[C:12]([NH:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][CH3:10])[CH2:1][CH2:2][CH3:3])[N:13]=1

참가 물질

4

반응물 2

HCID 5151220(2-Aminoethyl)dipropylamineHCID 119505673-Chloro-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazine 1-Oxide

생성물 1

HCID 11950566N1-(1-Oxido-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazin-3-yl)-N2,N2-dipropyl-1,2-ethanediamine수율 94%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

N,N-Dipropyl-1,2-ethanediamine (297) (0.53 g, 3.7 mmol) was added to a stirred solution of chloride 5 (325 mg, 1.5 mmol) in DME (30 mL) and the solution stirred at reflux temperature for 2 h. The solvent was evaporated and the residue was 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 10 (454 mg, 94%) as a pale yellow solid: mp (MeOH) 148-151° C.; 1H NMR δ 7.54 (d, J=8.4 Hz, 1H, H-6), 7.40 (d, J=8.4 Hz, 1H, H-5), 5.77 (br s, 1H, NH), 3.63-3.68 (m, 2H, H-9), 3.48-3.52 (m, 2H, CH2N), 2.95-3.00 (m, 2H, H-7), 2.68 (dd, J=6.0, 5.8 Hz, 2H, CH2N), 2.40-2.45 (m, 4H, 2×CH2N), 2.16-2.23 (m, 2H, H-8), 1.43-1.52 (m, 4H, 2×CH2), 0.90 (t, J=7.3 Hz, 6H, 2×CH3); 13C NMR δ 158.5, 149.0, 142.0, 137.3, 132.2, 129.2, 124.7, 55.9 (2), 52.6, 38.9, 35.3, 32.9, 24.8, 20.3 (2), 11.9 (2). Anal. calcd for C18H27N5O: C, 65.6; H, 8.3; N, 21.3. Found: C, 65.7; H, 8.6; N, 21.5%.

후처리

  1. temperatureat reflux temperature for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was 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-653e78cff9dc4df38dd9f911251c81f3
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

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