Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Trifluoroacetate | HCID 84468 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-Methyl-3-oxetanecarboxylic Acid | HCID 14028997 | — |
| Reactant | HCID 89443793 | HCID 89443793 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71533377 | HCID 71533377 | — |
Reaction Steps
To a 10° C. cold solution of 3-[1-(2,4-Difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile, trifluoroacetate (7c) (0.055 g, 0.118 mmol) in N,N-dimethylformamide (2 ml) was added triethylamine (18 μl, 0.13 mmol), 1-hydroxybenzotriazole (17 mg, 0.124 mmol), 3-methyl-3-oxetane carboxylic acid (13.8 mg) and finally 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (24 mg, 0.124 mmol). The mixture was allowed to warm to 25° C. and stirred for 16 h and purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 38 mg of 3-[1-(2,4-Difluoro-benzyl)-5-(3-methyl-oxetane-3-carbonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (8a).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09127001B2 |
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| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-68a62d35edc74101aebb72d9b3ddacfc |
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| Source note | uspto-grants-2015_09 |
|---|
