Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | HCID 68323812 | HCID 68323812 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 68324081 | HCID 68324081 | 11.3% |
Reaction Steps
Phenylmethyl 4-chloro-4-[({2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}amino)sulfonyl]-1-piperidinecarboxylate (Example 10) (80 mg, 0.133 mmol) was taken-up in EtOH (5 mL), MeOH (5 mL) and acetic acid (1 mL). 10% Palladium on carbon (14.19 mg, 0.013 mmol) was then added and the reaction mixture was stirred at RT under 2 Bar of hydrogen for 48 h. The reaction mixture was then filtered through celite and the celite was washed with 50 mL of MeOH. The solvent was concentrated to give a residue which was purified by normal phase chromatography, eluting with a gradient from 0-10% 2N NH3 in MeOH in DCM and then further purified by MDAP (basic conditions), to afford the title compound (7 mg). LCMS (A) m/z: 466 [M+1]+, Rt 0.81 min (basic).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09029545B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-7737ba9172ef4d599b806c893796f840 |
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| Source note | uspto-grants-2015_05 |
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