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

HRID 1669019Notes

Reaction equation

HRID 1669019 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH2:11][CH2:12]3)=[CH:8][C:6]=2[N:7]=1.CCN(CC)CC.[CH3:23][O:24][CH2:25][CH2:26][CH2:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>COCCOC>[CH3:23][O:24][CH2:25][CH2:26][CH2:27][N:28]([CH3:32])[CH2:29][CH2:30][NH:31][C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH2:11][CH2:12]3)=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-OxideHCID 54595302(2-Aminoethyl)(3-methoxypropyl)methylamine

Product 1

HCID 11950942N1-(3-Methoxypropyl)-N1-methyl-N2-(1-oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-1,2-ethanediamineYield 74%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 21 (1.62 g, 7.3 mmol), Et3N (2.0 mL, 14.0 mmol) and N1-(3-methoxypropyl)-N1-methyl-1,2-ethanediamine (274) (1.24 g, 8.8 mmol) in DME (50 mL) was heated at reflux temperature for 18 h. The solution was cooled, the solvent evaporated and the residue partitioned between dilute aqueous NH3 solution (50 mL) and DCM (50 mL). The aqueous layer was extracted with DCM (4×120 mL), the combined organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-15%) of MeOH/DCM, to give 1-oxide 32 (1.79 g, 74%) as a yellow solid: mp 41-42° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.39 (s, 1H, H-5), 5.83 (br s, 1H, NH), 3.55 (dt, J=5.9, 5.5 Hz, 2H, NCH2), 3.43 (t, J=6.3 Hz, 2H, OCH2), 3.33 (s, 3H, OCH3), 3.01 (t, J=7.4 Hz, 2H, H-8), 2.99 (t, J=7.8 Hz, 2H, H-6), 2.64 (t, J=5.9 Hz, 2H, NCH2), 2.50 (t, J=7.2 Hz, 2H, NCH2), 2.27 (s, 3H, NCH3), 2.14 (p, J=7.4 Hz, 2H, H-7), 1.76 (tt, J=7.2, 6.4 Hz, 2H, CH2); 13C NMR δ 158.7, 154.5, 148.8, 143.2, 129.8, 120.5, 114.7, 70.8, 58.6, 55.8, 54.4, 41.6, 38.6, 33.1, 32.3, 27.4, 25.7; MS (APCI) m/z 332 (MH+, 100%). Anal. calcd for C17H25N5O2: C, 61.6; H, 7.6; N, 21.1. Found: C, 61.4; H, 7.4; N, 21.4%.

Workup

  1. temperatureat reflux temperature for 18 h
  2. temperatureThe solution was cooled
  3. customthe solvent evaporated
  4. customthe residue partitioned between dilute aqueous NH3 solution (50 mL) and DCM (50 mL)
  5. extractionThe aqueous layer was extracted with DCM (4×120 mL)
  6. customthe combined organic fraction dried
  7. customthe solvent evaporated
  8. customThe residue was purified by chromatography
  9. washeluting with a gradient (0-15%) of MeOH/DCM

Sources & evidence

ORD record
ord-442b176926124f6d8ec3b4b968706dbb
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

Loading…