Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4-(Trifluoromethyl)benzaldehyde | HCID 67996 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 58654441 | HCID 58654441 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11690827 | HCID 11690827 | 7.5% |
Reaction Steps
To a solution of pyrrolidine-2-carboxylic acid (2-imidazol-1-yl-6-methyl-pyrimidin-4-ylmethyl)-amide (43 mg, 0.15 mmol) in dimethylformamide (1.5 mL) was added 4-(trifluoromethyl)benzaldehyde (22 μL, 0.16 mmol) and acetic acid (0.075 mL) at r.t. The solution was allowed to stir for 2 hrs. To the solution was added sodium triacetoxyborohydride (107 mg, 0.50 mmol) at r.t. The solution was stirred for 16 hrs then concentrated under vacuum. The residue was diluted with DCM, washed with NaOH (1N, 30 mL) and water (30 mL), dried over MgSO4, filtered and concentrated. The product was purified using mass-triggered LCMS to afford 5 mg of 1-(4-trifluoromethyl-benzyl)-pyrrolidine-2-carboxylic acid (2-imidazol-1-yl-6-methyl-pyrimidin-4-ylmethyl)-amide as a white solid. [M+H]+ 444.96.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07825256B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-8b3a22a836b14dbca891ab4b7872bc91 |
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| Source note | uspto-grants-2010_11 |
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