Sodium Bicarbonate → HCID 178439856, compound
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.CO[CH:22]([O:40]C)[CH2:23][NH:24][C:25]([C:27]1[CH:28]=[C:29]([CH3:39])[C:30]2[NH:34][C:33]([CH2:35][CH2:36][CH3:37])=[N:32][C:31]=2[CH:38]=1)=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:39][C:29]1[C:30]2[NH:34][C:33]([CH2:35][CH2:36][CH3:37])=[N:32][C:31]=2[CH:38]=[C:27]([C:25]2[O:40][CH:22]=[CH:23][N:24]=2)[CH:28]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
[step 2] To 7.7% phosphorus pentaoxide-methanesulfonic acid (Eaton's reagent; 10 mL) was added 6-(2,2-dimethoxyethylcarbamoyl)-4-methyl-2-propylbenzimidazole (400 mg, 1.31 mmol) obtained in step 1, and the mixture was stirred at 130° C. for 7 hr. The reaction solution was added to ice-cooled aqueous solution (100 mL), and the mixture was stirred for 30 min. After stirring, saturated aqueous sodium hydrogen carbonate solution (80 mL) and ethyl acetate (200 mL) were added to the mixture. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/80 to 0/100) to give the title compound (207 mg, 66%).
Workup
- additionThe reaction solution was added to ice-
- stirringthe mixture was stirred for 30 min
- stirringAfter stirring
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/80 to 0/100)
Sources & evidence
- ORD record
- ord-49c8086d430c4b0bb97fd28e38e97cb7
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486980B2
Reaction notes
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