Hydrogen Peroxide → HCID 68873219, compound

HRID 1770862Notes

Reaction equation

HRID 1770862 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)[C:15]([F:32])=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[OH:33]O>C1COCC1.C[Re](=O)(=O)=O>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([CH2:25][C:26]4[CH:31]=[CH:30][N+:29]([O-:33])=[CH:28][CH:27]=4)=[CH:23][CH:24]=3)[C:15]([F:32])=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 57562894HCID 57562894, compound

Product 1

HCID 68873219HCID 68873219, compound

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N2-(3-Aminosulfonylphenyl)-5-fluoro-N4-[4-(4-pyridylmethyl)phenyl]-2,4-pyrimidinediamine (50 mg) and methyltrioxorhenium (VII) (5 mg) in THF (15 mL) was treated with 30% aq. H2O2 (23 μL). After 24 h stirring, 30% aq. H2O2 (23 μL) was added and stirred for 24 h. The reaction mixture was filtered through Celite, washed the bed with methanol and concentrated. The residue was purified by HPLC yielded 10 mg of desired product. 1H NMR (DMSO d6, 300 MHz): δ 9.47 (s, 1H), 9.35 (s, 1H), 8.10 (m, 4H), 7.92 (m, 1H), 7.73 (d, 2H, J=8.4 Hz), 7.32-7.18 (m, 8H), 3.91 (s, 2H); LCMS (m/z): 467 (MH+).

Workup

  1. stirringstirred for 24 h
  2. filtrationThe reaction mixture was filtered through Celite
  3. washwashed the bed with methanol
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-362b07c6778b4f9792e68f9a19793819
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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