N,N-Diethylethylenediamine → HCID 11950762, compound

HRID 1669014Notes

Reaction equation

HRID 1669014 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].Cl[C:10]1[N:11]=[N+:12]([O-:23])[C:13]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][CH2:20]3)=[CH:16][C:14]=2[N:15]=1>COCCOC>[O-:23][N+:12]1[C:13]2[CH:22]=[C:21]3[C:17](=[CH:16][C:14]=2[N:15]=[C:10]([NH:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[N:11]=1)[CH2:18][CH2:19][CH2:20]3

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 11950762HCID 11950762, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N1,N1-Diethyl-1,2-ethanediamine (0.50 mL, 3.5 mmol) was added to a stirred solution of chloride 21 (314 mg, 1.4 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 2 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 26 (406 mg, 95%) as a yellow solid: mp (MeOH/EtOAc) 109-112° C.; 1H NMR δ 7.93 (s, 1H, H-9), 7.31 (s, 1H, H-5), 7.14 (br s, 1H, NH), 3.97-4.03 (m, 2H, CH2N), 3.42-3.46 (m, 2H, CH2N), 3.25-3.33 (m, 4H, 2×CH2N), 2.19-2.29 (m, 4H, H-6, H-8), 2.08-2.14 (m, 2H, H-7), 1.45 (t, J=7.3 Hz, 6H, 2×CH3); 13C NMR δ 158.2, 154.6, 148.4, 143.7, 129.8, 120.7, 114.4, 50.8, 47.7 (2), 36.3, 33.1, 32.3, 25.7, 8.8 (2). Anal. calcd for C16H23N5O: C, 63.8; H, 7.7; N, 23.2. Found: C, 63.9; H, 7.7; N, 23.3%.

Workup

  1. temperatureat reflux temperature for 2 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

Sources & evidence

ORD record
ord-72eb64863617497c90e9a96ad0d6c7e8
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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