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 1669080노트

반응식

HRID 1669080 반응식
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

참가 물질

5

반응물 3

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

생성물 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-ethanediamine수율 150.4%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-47648c88a1af4518bfcb33c6ffdbec29
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989451B2

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