HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → N3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-N7-(1-methylpyrrolidin-3-yl)imidazo[1,2-a]pyridine-3,7-dicarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | N3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-N7-(pyrrolidin-3-yl)imidazo[1,2-a]pyridine-3,7-dicarboxamide | HCID 67259833 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | N3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-N7-(1-methylpyrrolidin-3-yl)imidazo[1,2-a]pyridine-3,7-dicarboxamide | HCID 67259558 | 77.6% |
Reaction Steps
To N3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-N7-(pyrrolidin-3-yl)imidazo[1,2-a]pyridine-3,7-dicarboxamide (5 mg, 0.0096 mmol; prepared as in Example 46) in DCM/MeOH (1 mL/1 mL) was added HCHO as a 35% aqueous solution (16 mg, 0.19 mmol) and NaBH(OAc)3 (10 mg, 0.048 mmol). The reaction mixture was stirred for one hour, concentrated under reduced pressure and the residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to provide the final product (4 mg). MS (ES+APCI) m/z=537 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08841455B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-56f456b44d7c4334938db6f87b9e4332 |
| Source note | uspto-grants-2014_09 |