m-Chloroperbenzoic acid → HCID 11725253, compound

HRID 1813898Notes

Reaction equation

HRID 1813898 reaction equation
[C:1]1([S:7]([C:10]2[C:15](=[NH:16])[N:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]3=[N:12][C:11]=2[S:21][CH3:22])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)Cl>[C:1]1([S:7]([C:10]2[C:15](=[NH:16])[N:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]3=[N:12][C:11]=2[S:21]([CH3:22])=[O:28])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10286610HCID 10286610, compound

Product 1

HCID 11725253HCID 11725253, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Benzenesulfonyl-2-methylsulfanyl-pyrido[1,2-a]pyrimidin-4-ylideneamine (50 mg, 0.15 mmol) was dissolved in anhydrous methylenechloride (2 ml) to which 3-chloroperoxybenzoic acid powder (32 mg, 50-60%, ˜0.11 mmol) was added at 0° C. and stirred for 2 hours. In order to neutralize the reaction mixture, 2,6-tert-butyl-4-methylpyridine (38 mg, 90%, 0.17 mmol) was added. After concentration, the crude mixture was purified by preparative HPLC (XTerra™ MS C18 5.0 mM, MeOH/H2O as the eluent) to yield 26 mg of product as a pale yellow solid.

Workup

  1. additionwas added at 0° C.
  2. additionwas added
  3. concentrationAfter concentration
  4. customthe crude mixture was purified by preparative HPLC (XTerra™ MS C18 5.0 mM, MeOH/H2O as the eluent)

Sources & evidence

ORD record
ord-953d0c85ec3347f2b08fb8e2228095c0
Source dataset
uspto-grants-2005_04
Patent number
US06875771B2

Reaction notes

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