Triethylamine → HCID 11952179, compound

HRID 1669080Notes

Reaction equation

HRID 1669080 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.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21].CCN(CC)CC>COCCOC>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH:21][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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 119521783-Chloro-7-methyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 11952179HCID 11952179, compoundYield 150.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 95 (240 mg, 0.9 mmol), N1,N1-dimethyl-1,2-ethanediamine (0.26 mL, 2.4 mmol) and Et3N (0.33 mL, 2.4 mmol) in DME (50 mL) was stirred at reflux temperature for 4 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 96 (389 mg, 86%) as a yellow solid: mp (MeOH/EtOAc) 119-121° C.; 1H NMR δ 8.03 (s, 1H, H-9), 7.35 (s, 1H, H-5), 5.82 (br s, 1H, NH), 3.52-3.58 (m, 2H, CH2N), 3.07-3.17 (m, 2H, CH2), 2.55-2.67 (m, 5H, CH, CH2, CH2N), 2.28 [s, 6H, N(CH3)2], 1.15 (d, J=6.1 Hz, 3H, CH3); 13C NMR δ 158.7, 154.2, 148.9, 142.9, 129.8, 120.7, 114.8, 57.6, 45.1 (2), 41.2, 40.4, 38.7, 34.9, 20.2. Anal. calcd for C15H21N5O: C, 62.7; H, 7.4; N, 24.4. Found: C, 62.4; H, 7.1; N, 24.1%.

Workup

  1. temperatureat reflux temperature for 4 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-47648c88a1af4518bfcb33c6ffdbec29
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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