Hydrogen Peroxide → HCID 135526551, compound

HRID 1669037Notes

Reaction equation

HRID 1669037 reaction equation
OO.C(OC(C(F)(F)F)=O)(C(F)(F)F)=[O:4].[O:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][NH:25][C:26]2[N:27]=[N+:28]([O-:39])[C:29]3[CH:38]=[C:37]4[C:33]([CH2:34][CH2:35][CH2:36]4)=[CH:32][C:30]=3[N:31]=2)[CH2:18][CH2:17]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(Cl)(Cl)Cl.N>[O:16]1[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][NH:25][C:26]2[N:27]=[N+:28]([O-:39])[C:29]3[CH:38]=[C:37]4[C:33]([CH2:34][CH2:35][CH2:36]4)=[CH:32][C:30]=3[N+:31]=2[O-:4])[CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 11951287N-[2-(1,4-Oxazepan-4-yl)ethyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide

Product 1

HCID 135526551HCID 135526551, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

H2O2 (70%, 1.25 mL, ca. 25.8 mmol) was added dropwise to a stirred solution of TFAA (3.6 mL, 25.8 mmol) in DCM (35 mL) at 0° C. The solution was stirred at 20° C. for 10 min, then cooled to 0° C., added to a solution of 1-oxide 48 (0.85 g, 2.58 mmol) and TFA (0.43 mL, 5.50 mmol) in CHCl3 (35 mL) at 0° C. The solution was stirred at 20° C. for 5 h, diluted with dilute aqueous NH3 solution until basic and extracted with CHCl3 (4×60 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (3-6%) of MeOH/DCM, to give 1,4-dioxide 49 (0.37 g, 42%) as a red gum: 1H NMR δ 8.13 (s, 1H, H-9), 8.10 (s, 1H, H-5), 7.45 (br s, 1H, NH), 3.82 (t, J=6.1 Hz, 2H, CH2O), 3.74 (t, J=4.6 Hz, 2H, CH2O), 3.54 (q, J=5.7 Hz, 2H, NCH2), 2.97-3.04 (m, 4H, H-6, H-8), 2.73-2.80 (m, 6H, CH2), 2.15 (p, J=7.4 Hz, 2H, H-7), 1.91 (p, J=5.9 Hz, 2H, CH2); 13C NMR δ 158.7, 154.6, 148.8, 143.3, 129.8, 120.5, 114.7, 69.3, 68.7, 57.4, 55.8, 53.6, 38.7, 33.1, 32.3, 29.9, 25.7; HRMS (FAB+) calcd for C17H24N5O3 (MH+) m/z 346.1879, found 346.1877.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe solution was stirred at 20° C. for 5 h
  3. extractionextracted with CHCl3 (4×60 mL)
  4. customThe combined organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with a gradient (3-6%) of MeOH/DCM

Sources & evidence

ORD record
ord-2699224da6e7472abaab2c9df1630cfa
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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