N,N-Dimethylethylenediamine → HCID 25140917, compound

HRID 1669152Notes

Reaction equation

HRID 1669152 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:11]=[C:10]3[CH2:12][CH2:13][O:14][C:9]3=[CH:8][C:6]=2[N:7]=1.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH2:20]>COCCOC>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH:20][C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:11]=[C:10]3[CH2:12][CH2:13][O:14][C:9]3=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 25139754HCID 25139754, compound

Product 1

HCID 25140917HCID 25140917, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 206 (100 mg, 0.45 mmol) and N1,N1-dimethylethane-1,2-diamine (0.2 mL, 1.8 mmol) in DME (10 mL) was stirred at reflux temperature for 1 h, the solvent evaporated and the residue purified by chromatography, eluting with a gradient (5-8%) of MeOH/DCM to give the 1-oxide 207 (108 mg, 88%) as a yellow solid, mp 163-165° C.; 1H NMR δ 8.09 (t, J=1.4 Hz, 1H, H-9), 6.79 (s, 1H, H-5), 5.83 (br s, 1H, NH), 4.72 (t, J=8.3 Hz, 2H, H-7), 3.52-3.56 (m, 2H, CH2N), 3.31 (dt, J=8.3, 1.4 Hz, 2H, H-8), 2.57 (t, J=8.3 Hz, 2H, CH2N), 2.29 [s, 6H, N(CH3)2]; 13C NMR δ 166.5, 159.3, 151.8, 129.3, 126.4, 116.6, 102.0, 72.9, 57.6, 45.0 (2), 38.6, 28.6. HRMS (FAB+) calcd for C13H18N5O2 (MH+) m/z 276.1461, found 276.1461.

Workup

  1. temperatureat reflux temperature for 1 h
  2. customthe solvent evaporated
  3. customthe residue purified by chromatography
  4. washeluting with a gradient (5-8%) of MeOH/DCM

Sources & evidence

ORD record
ord-12c985d9d5444fcc9d40de77784b25dc
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

Loading…