Triethylamine → HCID 11950944, compound

HRID 1669021Notes

Reaction equation

HRID 1669021 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][NH2:31])[CH2:26]1>COCCOC>[CH3:23][O:24][CH:25]1[CH2:28][N:27]([CH2:29][CH2:30][NH:31][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 55285918HCID 55285918, compound

Product 1

HCID 11950944HCID 11950944, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 21 (1.32 g, 6.0 mmol), Et3N (1.65 mL, 11.8 mmol) and 2-(3-methoxy-1-azetidinyl)ethylamine (277) (950 mg, 7.3 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 (4×50 mL), the combined organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 34 (890 mg, 48%) as a yellow solid: mp 139-141° C.; 1H NMR δ 8.06 (s, 1H, H-9), 7.38 (s, 1H, H-5), 5.67 (br s, 1H, NH), 4.04 (p, J=5.8 Hz, 1H, CHO), 3.63-3.69 (m, 2H, CH2N), 3.47 (dt, J=5.9, 5.6 Hz, 2H, CH2N), 3.26 (s, 3H, OCH3), 2.93-3.03 (m, 6H, H-6, H-8, CH2N), 2.74 (t, J=5.9 Hz, 2H, NCH2), 2.14 (p, J=7.4 Hz, 2H, H-7); 13C NMR δ 158.7, 154.5, 148.7, 143.3, 129.8, 120.6, 114.6, 70.0, 61.4 (2), 58.0, 56.0, 39.3, 33.1, 32.3, 25.7; MS (APCI) m/z 316 (MH+, 100%). Anal. calcd for C16H21N5O2.¼H2O: C, 60.1; H, 6.8; N, 21.9. Found: C, 60.0; H, 6.6; N, 21.7%.

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 (4×50 mL)
  6. customthe combined organic fraction dried
  7. customthe solvent evaporated
  8. customThe residue was purified by chromatography
  9. washeluting with a gradient (0-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-babcd54a2205491ca37f80f68cc3f329
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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