Triethylamine → N-[4-(4-Morpholinyl)butyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide

HRID 1669053

반응식

HRID 1669053 반응식
[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:13]1[N:14]=[N+:15]([O-:26])[C:16]2[CH:25]=[C:24]3[C:20]([CH2:21][CH2:22][CH2:23]3)=[CH:19][C:17]=2[N:18]=1.CCN(CC)CC>COCCOC>[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:13]2[N:14]=[N+:15]([O-:26])[C:16]3[CH:25]=[C:24]4[C:20]([CH2:21][CH2:22][CH2:23]4)=[CH:19][C:17]=3[N:18]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2336114-(Morpholin-4-yl)butan-1-amineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

생성물 1

HCID 11951638N-[4-(4-Morpholinyl)butyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide수율 88%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

4-(4-Morpholinyl)butylamine (306) (2.02 g, 12.8 mmol) was added to a stirred solution of chloride 21 (1.89 g, 8.5 mmol) and Et3N (1.8 mL, 12.8 mmol) in DME (80 mL) and the solution stirred at reflux temperature for 16 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 62 (2.57 g, 88%) as pale yellow solid: mp (MeOH/EtOAc) 151-152° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.38 (s, 1H, H-5), 5.78 (br s, 1H, NH), 3.78 (br t, J=4.6 Hz, 4H, 2×CH2O), 3.50 (br dd, J=6.6, 5.9 Hz, 2H, CH2N), 2.95-3.02 (m, 4H, H-6, H-8), 2.45 (br t, J=4.4 Hz, 4H, 2×CH2N), 2.40 (t, J=7.0 Hz, 2H, CH2N), 2.15 (p, J=7.5 Hz, 2H, H-7), 1.67-1.74 (m, 2H, CH2), 1.58-1.64 (m, 2H, CH2); 13C NMR δ 158.8, 154.5, 148.8, 143.2, 129.8, 120.5, 114.7, 66.9 (2), 58.5, 53.7 (2), 41.3, 33.1, 32.3, 27.4, 25.7, 24.0. Anal. Calcd for C18H25N5O2: C, 63.0; H, 7.3; N, 20.4. Found: C, 62.9; H, 7.2; N, 20.5%.

후처리

  1. temperatureat reflux temperature for 16 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-c522c7aa0dea4528920f6c4468c0273e
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

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