HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → Tert-butyl(1-(2-(7-(hydroxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Tert-butyl (1-(2-(7-formyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate | HCID 86654350 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | Tert-butyl(1-(2-(7-(hydroxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate | HCID 131730903 | 29.2% |
Reaction Steps
To tert-butyl(1-(2-(7-formyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (10 mg, 0.021 mmol) in DCM/MeOH (1 mL/1 mL) was added NH3 in IPA (0.1 mL, 2M) and HOAc (0.2 mL), followed by NaB(OAc)3H (13 mg, 0.062 mmol). The reaction was stirred for 5 hours and then concentrated. The crude material was purified by silica gel chromatography (DCM/MeOH/NH4OH 20:1:0.1) to provide the desired product (3 mg). MS ESI (+) m/z 489 (M+1) detected.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895550B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-0282a01cc8ec4b15bf42c83c9a889cb5 |
| Source note | uspto-grants-2014_11 |