Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetaldehyde | HCID 177 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 4'-Fluoro-biphenyl-4-carboxylic acid [2-(methyl-pyrrolidin-3-ylmethyl-amino)-benzothiazol-6-yl]-amide | HCID 57771714 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 11562205 | HCID 11562205 | 78.2% |
Reaction Steps
Place 4′-fluoro-biphenyl-4-carboxylic acid [2-(methyl-pyrrolidin-3-ylmethyl-amino)-benzothiazol-6-yl]-amide (123 mg, 0.267 mmol) in THF (3 mL) and cool to 0° C. Add acetaldehyde (0.040 mL, 0.716 mmol) and sodium triacetoxyborohydride (88 mg, 0.415 mmol). Stir at 0° C. for 10 min. Dilute with DCM and wash with 1N NaOH. Collect the organic layer and chromatograph (silica gel, eluting with 10% 2M NH3 in MeOH:DCM) to yield 102 mg (78%) of the title compound: mass spectrum (ion-spray): (m/z)=489.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07838543B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-bef805b070a846b3b774ed05d83c172d |
|---|
| Source note | uspto-grants-2010_11 |
|---|