N,N-Diethylethylenediamine → HCID 25140478, compound

HRID 1669001Notes

Reaction equation

HRID 1669001 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[C:22]3[CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=[CH:16][C:14]=2[N:15]=1>COCCOC>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:10]1[N:11]=[N+:12]([O-:23])[C:13]2[C:22]3[CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:2]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 119505673-Chloro-8,9-dihydro-7H-indeno[5,4-e][1,2,4]triazine 1-Oxide

Product 1

HCID 25140478HCID 25140478, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N,N-Diethyl-1,2-ethanediamine (0.41 mL, 2.9 mmol) was added to a stirred solution of chloride 5 (215 mg, 1.0 mmol) in DME (30 mL) and the solution stirred at reflux temperature for 5 h. The solvent was evaporated and the residue was 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 8 (271 mg, 93%) as a pale yellow solid: mp (MeOH/EtOAc) 126-130° C.; 1H NMR δ 7.54 (d, J=8.4 Hz, 1H, H-6), 7.39 (d, J=8.4 Hz, 1H, H-5), 5.93 (br s, 1H, NH), 3.63 (br dd, J=7.5, 7.4 Hz, 2H, H-9), 3.52-3.57 (m, 2H, CH2N), 2.97 (br dd, J=7.8, 7.6 Hz, 2H, H-7), 2.74 (br t, J=6.0 Hz, 2H, CH2N), 2.63 (q, J=7.4 Hz, 4H, 2×CH2N), 2.16 (br p, J=7.6 Hz, 2H, H-8), 1.07 (t, J=7.1 Hz, 6H, 2×CH3); 13C NMR δ 158.4, 149.0, 142.0, 137.3, 132.2, 129.2, 124.6, 51.2, 46.6 (2), 38.5, 35.3, 32.8, 24.8, 11.5 (2). Anal. calcd for C16H23N5O.¼H2O: C, 62.8; H, 7.7; N, 22.9. Found: C, 63.0; H, 7.6; N, 22.9%.

Workup

  1. temperatureat reflux temperature for 5 h
  2. customThe solvent was evaporated
  3. customthe residue was 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-37c72e7456e440e883f53823c78cd5b5
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

Loading…