Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | N-(5-amino-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide | HCID 59511384 | — |
| Reactant | N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide | HCID 59513803 | — |
| Product | HCID 11512754 | HCID 11512754 | — |
Reaction Steps
The title compound was synthesized by combining N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (200 mg, 0.43 mmol) (prepared according to a procedure similar to that described in Example 27, Step C), N-(5-amino-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide (127 mg, 0.52 mmol), hydrochloric acid (0.043 mmol, 43 μL 1M HCl/diethylether) and 2 mL isopropanol in a sealed vessel. The vial and contents were heated in a microwave synthesizer at 180° C. for 30 min. The reaction was cooled and concentrated. The residue was partitioned between EtOAc and saturated NaHCO3. The organic was washed with brine, dried with MgSO4 and concentrated. The crude material was purified by silica gel column chromatography (0-100% gradient; (90% DCM:9% MeOH:1% NH4OH/DCM)). Purification provided 278 mg (95%) of the coupled adduct. ESIMS (M+H)+=684.20.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07812022B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-c9b3bdf7b0624bcf8f386933b0071919 |
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| Source note | uspto-grants-2010_10 |
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