1,2-Dimethoxyethane → HCID 11950940, compound

HRID 1669018Notes

Reaction equation

HRID 1669018 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.[CH3:16][O:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][NH:23]C.[CH3:25]OCCOC>>[O-:15][N+:4]1[C:5]2[CH:14]=[C:13]3[C:9](=[CH:8][C:6]=2[N:7]=[C:2]([NH:23][CH2:22][CH2:21][N:20]([CH2:19][CH2:18][O:17][CH3:16])[CH3:25])[N:3]=1)[CH2:10][CH2:11][CH2:12]3

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-OxideHCID 54809701HCID 54809701, compound

Product 1

HCID 11950940HCID 11950940, compoundYield 66%

Conditions

Temperature
20 °C

Procedure

A solution of the chloride 21 (2.0 g, 9.03 mmol) and N′-(2-methoxyethyl)-N1-methyl-1,2-ethanediamine (268) (2.38 g, 18.1 mmol) in DME (140 mL) was heated at reflux temperature for 22 h. The solution was cooled to 20° C., the solvent evaporated and the residue purified by column chromatography, eluting with a gradient (2-16%) of MeOH/DCM, to give 1-oxide 30 (1.89 g, 66%) as a yellow solid: mp 107-110° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.40 (s, 1H, H-5), 5.89 (br s, 1H, NH), 3.48-3.56 (m, 4H, CH2O, CH2N), 3.36 (s, 3H, OCH3), 3.00 (q, J=7.6 Hz, 4H, H-6, H-8), 2.63-2.71 (m, 4H, 2×CH2N), 2.33 (s, 3H, NCH3), 2.14 (p, J=7.4 Hz, 2H, H-7); 13C NMR δ 158.8, 154.4, 148.8, 143.1, 129.8, 120.5, 114.7, 71.0, 58.8, 56.7, 56.0, 42.4, 38.8, 33.1, 32.3, 25.7; HRMS (FAB+) calcd for C16H24N5O2 (MH+) m/z 318.1930, found 318.1930.

Workup

  1. temperatureat reflux temperature for 22 h
  2. customthe solvent evaporated
  3. customthe residue purified by column chromatography
  4. washeluting with a gradient (2-16%) of MeOH/DCM

Sources & evidence

ORD record
ord-8e9b697c1b3549f593eeb8a8fec8f116
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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