HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → Ivabradine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-3-(7,8-dimethoxy-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-N-methylpropanimidamide | HCID 66672603 | — |
| Reactant | Sodium tetraborohydride | HCID 131720822 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Ivabradine | HCID 132999 | 102.8% |
Reaction Steps
1 g of the product obtained in Step 1 (containing 46% amidine) is dissolved in 15 mL of methanol and then 86 mg (2.26 mmol, 1.2 equivalents) of sodium tetraborohydride are added at ambient temperature. Stirring is carried out overnight at ambient temperature, and then 5 mL of 20% aqueous sodium hydroxide solution and 20 mL of dichloromethane are added. Vigorous stirring is carried out for 15 minutes. The organic phase is then extracted, washed with water, dried over MgSO4, filtered and then evaporated to dryness. There is obtained 1 g of an oil which is purified by flash chromatography on 100 g of silica (eluant=dichloromethane/ethanol/NH4OH: 90/10/1) to yield 210 mg of the title product in the form of an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101747B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-2309f83711504d958037d1b325e95d79 |
| Source note | uspto-grants-2012_01 |