N,N-Dimethylethylenediamine → N1,N1-Dimethyl-N2-(1-oxido-7,8-dihydro-6H-chromeno[6,7-e][1,2,4]triazin-3-yl)-1,2-ethanediamine

HRID 1669174Notes

Reaction equation

HRID 1669174 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[N:9]=[N+:10]([O-:22])[C:11]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][CH2:18][O:19]3)=[CH:14][C:12]=2[N:13]=1>COCCOC>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:8]1[N:9]=[N+:10]([O-:22])[C:11]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][CH2:18][O:19]3)=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 251398843-Chloro-7,8-dihydro-6H-chromeno[6,7-e][1,2,4]triazine 1-Oxide

Product 1

HCID 25138708N1,N1-Dimethyl-N2-(1-oxido-7,8-dihydro-6H-chromeno[6,7-e][1,2,4]triazin-3-yl)-1,2-ethanediamineYield 84.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N,N-Dimethyl-1,2-ethanediamine (0.47 mL, 4.3 mmol) was added to a stirred solution of chloride 240 (341 mg, 1.4 mmol) in DME (30 mL) and the solution 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 241 (343 mg, 83%) as a yellow solid: mp (MeOH/EtOAc) 150-152° C.; 1H NMR δ 7.58 (s, 1H, H-10), 7.30 (s, 1H, H-5), 5.79 (br s, 1H, NH), 4.25 (br dd, J=5.3, 5.2 Hz, 2H, H-8), 3.51-3.56 (m, 2H, CH2N), 2.96 (br t, J=6.0 Hz, 2H, H-6), 2.60 (br t, J=6.0 Hz, 2H, CH2N), 2.31 [s, 6H, N(CH3)2], 2.02-2.09 (m, 2H, H-7); 13C NMR δ 158.0, 152.9, 143.6, 135.1, 130.0, 126.1, 104.3, 66.9, 57.6, 45.0 (2), 38.7, 25.9, 21.7. Anal. calcd for C14H19N5O2.½H2O: C, 57.2; H, 6.7; N, 23.8. Found: C, 57.1; H, 6.5; N, 23.9%.

Workup

  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

Sources & evidence

ORD record
ord-19304c818c2845bcab30da494ee195f0
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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