HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → {6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 1-Phenyl-1H-pyrazole-3-carbaldehyde | HCID 13432476 | — |
| Reactant | (8-[1,4]Diazepan-1-yl-6-methyl-quinolin-7-yloxy)-acetic acid ethyl ester | HCID 59366177 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | {6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid ethyl ester | HCID 59366193 | 57.3% |
Reaction Steps
A mixture of (8-[1,4]diazepan-1-yl-6-methyl-quinolin-7-yloxy)-acetic acid ethyl ester (600 mg, 1.75 mmol), 1-Phenyl-1H-pyrazole-3-carbaldehyde (300.8 mg, 1.75) and NaBH(OAc)3 (408 mg, 1.92 mmol) in DCE (5 ml) was stirred at rt for 3 hrs. The reaction was then diluted with DCE (20 ml), filtered, and purified by flash column chromatography on silica gel to give the desired product (500 mg, 57%). MS (ES) m/z 500.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08853202B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-4a232e139c964bfdb8e4eb8968899491 |
| Source note | uspto-grants-2014_10 |