Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 86681281 | HCID 86681281 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67996739 | HCID 67996739 | 68.8% |
Reaction Steps
LiOH (1M, aqueous) (3.0 ml, 3.00 mmol) was added to a stirred mixture of (2S,5R)-methyl 1-(2-fluoro-6-methoxybenzyl)-5-(3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamido)piperidine-2-carboxylate (1 g, 1.881 mmol) in THF (30 ml) & MeOH (10 ml) and the mixture was stirred at room temperature for Overnight. The reaction LCMS showed most starting material (M+1=532), but tlc showed product, another 3 ml of LiOH was added to the r×n, stirred for one day, LCMS gave M+H at 518, tlc showed completion. The reaction was treated 1 N HCl in ether, 6 ml, 1 eq, and rotovap to dryness and the residue was purified by column chromatography on silica gel Biotage 40M, eluting with 20% MeOH/CH2Cl2 to give the titled compound as a off-white (0.67 g, 68.8% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08999957B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-75fdcbf7899742b8847411b98fbbaeac |
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| Source note | uspto-grants-2015_04 |
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