Hydrogen Peroxide → HCID 66712056, compound

HRID 1262373Notes

Reaction equation

HRID 1262373 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[N:20]3[C:15]([CH:16]=[N:17][C:18](O)=[N:19]3)=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[CH2:22]([S:24](C1C=C(C2N3C(C=NC(SC)=N3)=CC=2)C=CC=1)(=[O:26])=[O:25])C.OO.[O-]S([O-])(=S)=O.[Na+].[Na+]>CO.CC(O)=O>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[N:20]3[C:15]([CH:16]=[N:17][C:18]([S:24]([CH3:22])(=[O:26])=[O:25])=[N:19]3)=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 24477Sodium ThiosulfateHCID 66712670HCID 66712670, compoundHCID 178477631HCID 178477631, compound

Product 1

HCID 66712056HCID 66712056, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

7-(3-Ethanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol: To a mixture of Na2WO4.2H2O (62 mg, 0.19 mmol) and 7-(3-Ethanesulfonyl-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (1.25 g, 3.76 mmol) in methanol (40.0 mL) was added 50% H2O2 (0.65 mL, 11 mmol) and the reaction was stirred at 60° C. for 5 h. The mixture was treated with HOAc (700 uL), 50% H2O2 (0.65 mL, 11 mmol) and Na2WO4.2H2O (65 mg, 0.2 mmol) and warmed at 60° C. until reaction was completed as analyzed by LC/MS. At this time, the mixture was treated with 10% aqueous solution of Na2S2O3 (5 mL) and the resultant solids were collected on a Buchner funnel, washed with water (5×5 mL) and dried in vacuo to afford 7-(3-ethanesulfonyl-phenyl)-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine (1.33 g; Yield=97%, HPLC RT=2.51). To the above sulfone in 1,4-dioxane (4 mL) and DMSO (2.5 mL) was added an aqueous solution of 5N NaOH (11.1 mL, 55.4 mmol). The mixture was heated at 80° C., O/N, cooled in an ice bath and treated with 3M HCl until pH 4. The resulting solids were collected on a Buchner funnel, washed with water (5×5 mL) and dried in vacuo to afford the title compound (0.675 g; Yield=88%). LC/MS: 304 (M+H); HPLC: RT=1.81 min; 1H NMR: (DMSO, δ) 11.88 (br s, 1H), 9.05 (s, 1H), 8.68 (s, 1H), 8.59 (d, J=7.7, 1H), 7.87 (d, J=7.7, 1H), 7.80 (t, 1H, J=7.7), 7.45 (d, J=4.9, 1H), 7.06 (d, J=4.9, 1H), 3.39 (q, J=7.2, 2H), 1.15 (t, J=7.2, 3H).

Workup

  1. temperaturewarmed at 60° C. until reaction
  2. customthe resultant solids were collected on a Buchner funnel
  3. washwashed with water (5×5 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-47a9d22b8f6e408f8eb8f7653dd04404
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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