Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ammonium formate | HCID 2723923 | — |
| Reactant | HCID 69820417 | HCID 69820417 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | HCID 69820673 | HCID 69820673 | 75% |
Reaction Steps
A mixture of 0.2 g (0.3 mmol) of (S)-N-[2-[[[4-(6-aminopyrid-3-yl)-1-[(4-ethylpiperid-3-yl)carbonyl]butyl]amino]sulphonyl]-4-bromo-6-pyrid-2-ylphenyl]propanamide, 0.02 g of active 10% palladium-on-charcoal and 0.2 g of ammonium formate (3.0 mmol) in 10 ml of methanol is refluxed for 2 h. The reaction mixture is filtered and is then taken up in 100 ml of dichloromethane, washed with 50 ml of saturated sodium hydrogen carbonate solution and 50 ml of saturated sodium chloride solution. The resulting solution is dried over sodium sulphate and then filtered and the resulting product is concentrated. The residue thus obtained is taken up in 40 ml of a 0.1N solution of hydrogen chloride in isopropanol and is then concentrated and purified by chromatography on an RP18 column, eluting with an acetonitrile/water gradient of from 5/95 to 30/70. 0.135 g of (S)-N-[2-[[[4-(6-aminopyrid-3-yl)-1-[(4-ethylpiperid-3-yl)carbonyl]butyl]amino]sulphonyl]-6-pyrid-2-ylphenyl]propanamide hydrochloride (2:1) is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06680329B2 |
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| Source dataset | uspto-grants-2004_01 |
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| ORD ID | ord-390c21f0187042d0bcf0128f5e037c02 |
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| Source note | uspto-grants-2004_01 |
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