Triethylamine → 7-Methyl-N-[3-(4-morpholinyl)propyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide

HRID 1669083Notes

Reaction equation

HRID 1669083 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:16])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH:11]([CH3:15])[CH2:12]3)=[CH:8][C:6]=2[N:7]=1.[N:17]1([CH2:23][CH2:24][CH2:25][NH2:26])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.CCN(CC)CC>COCCOC>[CH3:15][CH:11]1[CH2:10][C:9]2[C:13](=[CH:14][C:5]3[N+:4]([O-:16])=[N:3][C:2]([NH:26][CH2:25][CH2:24][CH2:23][N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[N:7][C:6]=3[CH:8]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61055N-(3-Aminopropyl)morpholineHCID 119521783-Chloro-7-methyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 119521817-Methyl-N-[3-(4-morpholinyl)propyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-OxideYield 98%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 95 (367 mg, 1.6 mmol), 3-(4-morpholinyl)propylamine (0.34 mL, 2.3 mmol) and Et3N (0.33 mL, 2.3 mmol) in DME (50 mL) was stirred at reflux temperature for 8 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 98 (525 mg, 98%) as a yellow solid: mp (MeOH/DCM) 138-140° C.; 1H NMR δ 8.04 (s, 1H, H-9), 7.35 (s, 1H, H-5), 6.10 (br t, J=5.0 Hz, 1H, NH), 3.75 (br t, J=4.7 Hz, 4H, 2×CH2O), 3.56-3.61 (m, 2H, CH2N), 3.08-3.18 (m, 2H, CH2), 2.56-2.65 (m, 3H, CH, CH2), 2.44-2.52 (m, 6H, 3×CH2N), 1.83 (br p, J=6.5 Hz, 2H, CH2), 1.15 (d, J=6.1 Hz, 3H, CH3); 13C NMR δ 158.8, 154.2, 148.9, 142.8, 129.8, 120.7, 114.8, 67.0 (2), 57.3, 53.8 (2), 41.2, 40.8, 40.4, 34.9, 25.3, 20.4. Anal. calcd for C18H25N5O2: C, 63.0; H, 7.3; N, 20.4. Found: C, 63.2; H, 7.2; N, 20.4%.

Workup

  1. temperatureat reflux temperature for 8 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-66b2ae6460204e84954b68ac076fe78e
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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