3-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide → HCID 11951460, compound

HRID 1669041Notes

Reaction equation

HRID 1669041 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][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][NH2:24]>COCCOC>[CH3:16][O:17][CH2:18][CH2:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][NH:24][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

4

Reactant 2

HCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-OxideHCID 28387859(3-aminopropyl)(2-methoxyethyl)methylamine

Product 1

HCID 11951460HCID 11951460, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 21 (2.0 g, 9.03 mmol) and N1-(2-methoxyethyl)-N1-methylpropane-1,3-diamine (297) (2.0 g, 13.6 mmol) in DME (140 mL) was stirred at 20° C. for 18 h, the solvent evaporated and the residue purified by column chromatography, eluting with a gradient (2-15%) of MeOH/DCM, to give 1-oxide 52 (2.3 g, 79%) as a yellow solid: mp 59-61° C.; 1H NMR [(CH3)2SO] δ 7.94 (s, 1H, H-9), 7.68 (br s, 1H, NH), 7.38 (s, 1H, H-5), 3.24-3.44 (m, 6H, CH2), 3.23 (s, 3H, OCH3), 2.92-2.99 (m, 4H, H-6, H-8), 2.56 (br t, J=5.8 Hz, 2H, CH2N), 2.24 (s, 3H, NCH3), 2.03-2.07 (m, 2H, H-7), 1.70-1.74 (m, 2H, CH2); HRMS (FAB+): calcd for C17H26N5O2 (MH+) m/z 332.2087, found, 332.2089.

Workup

  1. customthe solvent evaporated
  2. customthe residue purified by column chromatography
  3. washeluting with a gradient (2-15%) of MeOH/DCM

Sources & evidence

ORD record
ord-176c919812f240ac8a2e29d3401625f1
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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