m-Chloroperbenzoic acid → 1H-Benzimidazole, 1-methyl-

To a solution of trans-2-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(methylthio)pyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (1-5) (250 mg, 0.64 mmol, 1.0 eq.) in CH2Cl2 (5.0 mL) was added meta-chloroperbenzoic acid (274 mg, 1.59 mmol, 2.5 eq.) at room temperature and the reaction was stirred for 3 hours. The reaction was quenched by addition of saturated sodium bicarbonate solution (10 mL) and extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by silica gel column chromatography (100% ethyl acetate) to afford trans-2-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(methylsulfonyl)pyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (1-6) as a pale yellow foam. 1H NMR (300 MHz, CDCl3) δ 8.10 (s, 1H), 7.72-7.67 (m, 1H), 7.34-7.23 (m, 3H), 3.84 (s, 3H), 3.38 (s, 3H), 3.11-3.03 (m, 1H), 2.96 (s, 3H), 2.96-2.87 (m, 1H), 2.42 (s, 3H), 2.18-2.06 (m, 2H). LRMS m/z (M+H) 424 found, 424 required.

1. customThe reaction was quenched by addition of saturated sodium bicarbonate solution (10 mL)
2. extractionextracted with CH2Cl2 (2×10 mL)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated to dryness
6. customThe residue was purified by silica gel column chromatography (100% ethyl acetate)

ORD record

ord-191632fd5b604df49eaeeb2fe07bdf90

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200001B2