Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Carboxybenzaldehyde | HCID 12077 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | N-(Piperidin-3-yl)isoquinolin-5-amine--hydrogen chloride (1/1) | HCID 69523874 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 70980589 | HCID 70980589 | 74.5% |
Reaction Steps
To a solution of Intermediate 4 (10 g×2, 0.0379 mol×2) in DCE (400 mL×2) was added Et3N (9.2 g×2, 0.0910 mol×2) and MgSO4 (20×2, 0.139 mol×2), and stirred for 0.5 h at 30° C. 3-formylbenzoic acid (6.26 g×2, 0.0417 mol×2) and AcOH (5.46 g×2, 0.0910 mol×2) was added. The reaction mixture was stirred at 30° C. for 0.5 hours. NaBH(OAc)3 (24.1 g×2, 0.1137 mol×2) was added and the reaction mixture was stirred at 30° C. overnight. TLC (methylene dichloride:methanol=10:1) showed the reaction was complete. The reaction mixture was filtered. The filtered cake was washed with CH2Cl2, the filtrate was washed with brine, dried over Na2SO4 and concentrated in vacuo, and purified by preparative HPLC to give Intermediate 5 (10.2 g, 37.2%) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09073905B2 |
|---|
| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-79f6d6892ee54dd4b11656131fe20c12 |
|---|
| Source note | uspto-grants-2015_07 |
|---|
