Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | HCID 67053021 | HCID 67053021 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 44544091 | HCID 44544091 | 48.2% |
Reaction Steps
To a vial was added {4-[6-(2-{[1-dimethylaminomethylidene]sulfamoyl}phenyl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]-6-ethanesulfonylpyridin-3-yl}carbamic acid tert-butyl ester (48 mg, 0.07 mmol) in 3 mL of methanol, followed by the addition of DBU (106 mg, 0.7 mmol). The reaction mixture was stirred at 70° C. for 90 minutes. To the reaction was added 0.5 mL of water, and the reaction mixture was stirred at 70° C. for 1.5 hours. The reaction mixture was concentrated in vacuo. The crude mixture was purified by flash chromatography. The column was eluted with 0-5% MeOH/CH2Cl2 to afford 18 mg (48%) of 2-[3-(5-ethanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl]benzenesulfonamide. MS (ES+) m/z 534 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08268859B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-49b08bb30aea453682468ecf943447e0 |
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| Source note | uspto-grants-2012_09 |
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