Triethylamine → HCID 11951462, compound

HRID 1669043Notes

Reaction equation

HRID 1669043 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.CCN(CC)CC.[CH3:23][O:24][CH:25]1[CH2:28][N:27]([CH2:29][CH2:30][CH2:31][NH2:32])[CH2:26]1>COCCOC>[CH3:23][O:24][CH:25]1[CH2:28][N:27]([CH2:29][CH2:30][CH2:31][NH:32][C:2]2[N:3]=[N+:4]([O-:15])[C:5]3[CH:14]=[C:13]4[C:9]([CH2:10][CH2:11][CH2:12]4)=[CH:8][C:6]=3[N:7]=2)[CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-OxideHCID 55285919HCID 55285919, compound

Product 1

HCID 11951462HCID 11951462, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 21 (1.33 g, 6.0 mmol), Et3N (1.7 mL, 12 mmol) and 3-(3-methoxy-1-azetidinyl)propylamine (299) (1.2 g, 8.4 mmol) in DME (30 mL) was heated at reflux temperature for 18 h. The solution was cooled, the solvent evaporated and the residue partitioned between dilute aqueous NH3 solution (50 mL) and DCM (50 mL). The aqueous layer was extracted with DCM (2×25 mL), the combined organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-15%) of MeOH/DCM, to give 1-oxide 54 (1.32 g, 66%) as a yellow solid: mp 101-102° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.39 (s, 1H, H-5), 6.18 (br s, 1H, NH), 4.07 (p, J=5.9 Hz, 1H, CHO), 3.65-3.71 (m, 2H, CH2N), 3.54 (dt, J=6.2, 5.8 Hz, 2H, CH2N), 3.26 (s, 3H, OCH3), 2.94-3.04 (m, 4H, H-6, H-8), 2.82-2.88 (m, 2H, CH2N), 2.63 (t, J=6.4 Hz, 2H, CH2N), 2.14 (p, J=7.1 Hz, 2H, H-7), 1.70 (p, J=6.4 Hz, 2H, CH2); 13C NMR δ 158.8, 154.5, 148.8, 143.1, 129.8, 120.6, 114.7, 69.7, 61.5 (2), 58.6, 56.0, 40.8, 33.1, 32.3, 26.6, 25.8; MS (APCI) m/z 330 (MH+, 100%). Anal. calcd for C17H23N5O2: C, 62.0; H, 7.0; N, 21.3. Found: C, 61.7; H, 7.2; N, 21.2%.

Workup

  1. temperatureat reflux temperature for 18 h
  2. temperatureThe solution was cooled
  3. customthe solvent evaporated
  4. customthe residue partitioned between dilute aqueous NH3 solution (50 mL) and DCM (50 mL)
  5. extractionThe aqueous layer was extracted with DCM (2×25 mL)
  6. customthe combined organic fraction dried
  7. customthe solvent evaporated
  8. customThe residue was purified by chromatography
  9. washeluting with a gradient (0-15%) of MeOH/DCM

Sources & evidence

ORD record
ord-5f3ff0f8bb2441a58e69dd3d2270cbb4
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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