Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 59588794 | HCID 59588794 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 16747642 | HCID 16747642 | 54.6% |
Reaction Steps
To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzothiazole-6-carboxaldehyde (500 mg, 1.7 mmol) in MeOH (14 mL) and THF (28 mL) was added pyrrolidine (242 mg, 3.4 mmol), acetic acid (22 mg, 0.4 mmol) and NaCNBH3 (158 mg, 2.7 mmol). The mixture was stirred at 63° C. overnight. Then the mixture was concentrated under reduced pressure and dichloromethane (15 mL) was added. The mixture was washed with brine and the organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 318 mg (27%) of 2-(4-cyclopropylpiperazin-1-yl)-6-(pyrrolidin-1-ylmethyl)-benzothiazole as a trifluoroacetate salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08394842B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-7920a9a93e8b4fbf9622c711f92edfcd |
|---|
| Source note | uspto-grants-2013_03 |
|---|