HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → Ethyl 8-(1-acetyl-piperidin-4-yl)amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | N-Acetyl-4-piperidone | HCID 122563 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate | HCID 24993827 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ethyl 8-(1-acetyl-piperidin-4-yl)amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate | HCID 45141159 | 70% |
Reaction Steps
To a suspension of 5.187 g (19 mmol) of ethyl 8-amino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in dry dimethylformamide (120 mL), were added 1-acetyl-4-piperidone (4.7 mL, 38 mmol), CF3COOH (10 mL, 128 mmol) and NaBH(OAc)3 (8.862 g, 42 mmol). After 18 hours, NaOH 0.33N (800 mL, 264 mmol) was added dropwise to the mixture. The precipitate was filtered, washed with water and dried in oven to dryness to give 5.3 g (70% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08541429B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-061067fb3a22442db40a376ffbe1000a |
| Source note | uspto-grants-2013_09 |