Triethylamine → HCID 11951466、化合物

HRID 1669048

反応式

HRID 1669048 の反応式
[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

参加物

5

反応物 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

生成物 1

HCID 11951466HCID 11951466、化合物収率 84%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-f38ee3e928be47a885c7c282d7d29d58
出典データセット
uspto-grants-2011_08
特許番号
US07989451B2

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