Benzimidazole → HCID 67221594, compound

Temperature

160 °C

Charged benzimidazole (III) (28.98 mmoles), cesium carbonate (33.81 mmoles), cuprous oxide (0.918 mmoles), 2-amino-4,6-dihydroxypyrimidine (3.62 mmoles), PEG (28.98 mmoles), 5-bromo-thiophen-2-carboxylic acid (IV)(24.15 mmoles) and NMP (10 ml) to the 100 ml RB flask fitted with thermo well and condenser. The reaction mixture was heated to 160° C. and maintained for 18-20 hrs. After completion of reaction, cooled the reaction to room temperature, added water (100 ml) and adjusted the pH to ˜4.5-5 using formic acid. Filtered off the precipitated solid and washed with water (2×25 ml). The solid was then dissolved in methanol (250 ml), filtered through a celite bed, distilled of the solvent completely under reduced pressure. To the residue IPA (25 ml) was added to precipitate the product, stirred for 30 min, filtered and dried to get the compound (V).

1. customfitted with thermo well and condenser
2. temperaturemaintained for 18-20 hrs
3. customAfter completion of reaction
4. temperaturecooled
5. customthe reaction to room temperature
6. filtrationFiltered off the precipitated solid
7. washwashed with water (2×25 ml)
8. dissolutionThe solid was then dissolved in methanol (250 ml)
9. filtrationfiltered through a celite bed
10. distillationdistilled of the solvent completely under reduced pressure
11. additionTo the residue IPA (25 ml) was added
12. customto precipitate the product
13. filtrationfiltered
14. customdried

ORD record

ord-84f2fb1a55b34ed8adeef1b905f32215

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703811B2