Triethylamine → N1,N1-Dimethyl-N2-(7-methyl-1 oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-1,2-ethanediamine

HRID 1669080ノート

反応式

HRID 1669080 の反応式
Cl[C:2]1[N:3]=[N+:4]([O-:16])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH:11]([CH3:15])[CH2:12]3)=[CH:8][C:6]=2[N:7]=1.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21].CCN(CC)CC>COCCOC>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH:21][C:2]1[N:3]=[N+:4]([O-:16])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH:11]([CH3:15])[CH2:12]3)=[CH:8][C:6]=2[N:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 119521783-Chloro-7-methyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

生成物 1

HCID 11952179N1,N1-Dimethyl-N2-(7-methyl-1 oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-1,2-ethanediamine収率 150.4%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of chloride 95 (240 mg, 0.9 mmol), N1,N1-dimethyl-1,2-ethanediamine (0.26 mL, 2.4 mmol) and Et3N (0.33 mL, 2.4 mmol) in DME (50 mL) was stirred at reflux temperature for 4 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 96 (389 mg, 86%) as a yellow solid: mp (MeOH/EtOAc) 119-121° C.; 1H NMR δ 8.03 (s, 1H, H-9), 7.35 (s, 1H, H-5), 5.82 (br s, 1H, NH), 3.52-3.58 (m, 2H, CH2N), 3.07-3.17 (m, 2H, CH2), 2.55-2.67 (m, 5H, CH, CH2, CH2N), 2.28 [s, 6H, N(CH3)2], 1.15 (d, J=6.1 Hz, 3H, CH3); 13C NMR δ 158.7, 154.2, 148.9, 142.9, 129.8, 120.7, 114.8, 57.6, 45.1 (2), 41.2, 40.4, 38.7, 34.9, 20.2. Anal. calcd for C15H21N5O: C, 62.7; H, 7.4; N, 24.4. Found: C, 62.4; H, 7.1; N, 24.1%.

後処理

  1. temperatureat reflux temperature for 4 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-47648c88a1af4518bfcb33c6ffdbec29
出典データセット
uspto-grants-2011_08
特許番号
US07989451B2

反応ノート

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