Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Bis(2-oxo-3-oxazolidinyl)phosphinic chloride | HCID 152842 | — |
| Reactant | (2R)-2-methoxypropanoic acid | HCID 2733584 | — |
| Reactant | HCID 60205313 | HCID 60205313 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 60205634 | HCID 60205634 | 70% |
Reaction Steps
TEA (0.82 mL, 5.91 mmol) was added to a mixture of 4,5-difluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.20 g, 1.18 mmol; Example 13, Step C), (R)-2-methoxypropanoic acid (0.25 g, 2.37 mmol) and BOP-Cl (0.60 g, 2.37 mmol) in DCM (5 mL) at room temperature. The reaction was stirred at room temperature for 1 hour, and then a 2N LiOH solution (3 mL) was added. The mixture was stirred at room temperature for 30 minutes, and water (10 mL) and ethyl acetate (30 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by chromatography on silica gel (hexane:ethyl acetate 1:2) to give (R)-N-(4,5-difluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxypropanamide (0.21 g, 70%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178131B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-699a8b00e5be4a88b1c1f1c87717bb85 |
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| Source note | uspto-grants-2012_05 |
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