Ammonia → HCID 178438083, compound

HRID 1669099Notes

Reaction equation

HRID 1669099 reaction equation
OO.[CH3:3][N:4]([CH3:21])[CH:5]1[CH2:20][C:19]2[C:7](=[CH:8][C:9]3[N+:14]([O-:15])=[N:13][C:12]([CH2:16][CH3:17])=[N:11][C:10]=3[CH:18]=2)[CH2:6]1.C(O)(C(F)(F)F)=[O:23].N>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:21][N:4]([CH3:3])[CH:5]1[CH2:20][C:19]2[C:7](=[CH:8][C:9]3[N+:14]([O-:15])=[N:13][C:12]([CH2:16][CH3:17])=[N+:11]([O-:23])[C:10]=3[CH:18]=2)[CH2:6]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 119523627-(Dimethylamino)-3-ethyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 178438083HCID 178438083, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

H2O2 (70%, 0.47 mL, ca. 9.7 mmol) was added dropwise to a stirred solution of TFM (1.35 mL, 9.7 mmol) in DCM (15 mL) at 0° C. The solution was stirred at 20° C. for 10 min, then cooled to 0° C. and added to a solution of 1-oxide 115 (250 mg, 0.97 mmol) and TFA (0.16 mL, 2.07 mmol) in CHCl3 (15 mL) at 0° C. The solution was stirred at 20° C. for 5 h. The solution was made basic with dilute aqueous NH3 solution and extracted with CHCl3 (3×30 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by column chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1,4-dioxide 116 (55 mg, 21%) as an unstable brown solid: 1H NMR δ 8.30 (s, 1H, H-9), 8.25 (s, 1H, H-5), 3.07-3.37 (m, 7H, H-6, H-7, H-8, CH2), 2.36 [s, 6H, N(CH3)2], 1.43 (t, J=7.5 Hz, 3H, CH3); HRMS calcd for C14H18N4O2 (M+) m/z 274.1430, found 274.1428.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe solution was stirred at 20° C. for 5 h
  3. extractionextracted with CHCl3 (3×30 mL)
  4. customThe combined organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with a gradient (0-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-e01c65435cba4846be5b21162c6c6d4e
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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