Triethylamine → HCID 11951466, 화합물

HRID 1669048

반응식

HRID 1669048 반응식
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][NH2:12])[CH2:5][CH2:4]1.Cl[C:14]1[N:15]=[N+:16]([O-:27])[C:17]2[CH:26]=[C:25]3[C:21]([CH2:22][CH2:23][CH2:24]3)=[CH:20][C:18]=2[N:19]=1.CCN(CC)CC>COCCOC>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][NH:12][C:14]2[N:15]=[N+:16]([O-:27])[C:17]3[CH:26]=[C:25]4[C:21]([CH2:22][CH2:23][CH2:24]4)=[CH:20][C:18]=3[N:19]=2)[CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-OxideHCID 433726333-(4-Methoxypiperidin-1-yl)propan-1-amine

생성물 1

HCID 11951466HCID 11951466, 화합물수율 84%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

3-(4-Methoxy-1-piperidinyl)propylamine (304) (0.59 g, 3.4 mmol) was added to a stirred solution of chloride 21 (505 mg, 2.3 mmol) and Et3N (0.64 mL, 2.6 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 16 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 58 (681 mg, 84%) as a yellow solid: mp (EtOAc/pet. ether) 120-121° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.38 (s, 1H, H-5), 6.25 (br s, 1H, NH), 3.56-3.61 (m, 2H, CH2N), 3.33 (s, 3H, OCH3), 3.24-3.30 (m, 1H, CHO), 2.97-3.03 (m, 4H, H-6, H-8), 2.71-2.78 (m, 2H, CH2N), 2.52 (br t, J=6.6 Hz, 2H, CH2N), 2.21-2.30 (m, 2H, CH2), 2.15 (br p, J=7.5 Hz, 2H, H-7), 1.91-1.98 (m, 2H, CH2), 1.85 (br p, J=6.5 Hz, 2H, CH2), 1.65-1.73 (m, 2H, CH2); 13C NMR δ 158.8, 154.4, 148.8, 143.0, 129.8, 120.5, 114.7, 75.8, 56.8, 55.5, 50.9 (2), 40.9, 33.1, 32.3, 30.5 (2), 25.7 (2). Anal. calcd for C19H27N5O2: C, 63.8; H, 7.6; N, 19.6. Found: C, 63.6; H, 7.6; N, 19.4%.

후처리

  1. temperatureat reflux temperature for 16 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-f38ee3e928be47a885c7c282d7d29d58
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

연결된 노트

불러오는 중…