Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Butyl chloroformate | HCID 61140 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline | HCID 66709668 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68560613 | HCID 68560613 | 43% |
Reaction Steps
Diisopropylethylamine (186 μL, 1.07 mmol) and butyl chloroformate (51 μL, 0.40 mmol) were added at 0° C. to a dichloromethane (5 mL) solution of the 5-(methylsulfonyl)-1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]indoline (100 mg, 0.267 mmol) produced in Reference Example 28, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, water was added, followed by extraction with ethyl acetate three times. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-1:2, V/V) to obtain the title compound as white powder (53.9 mg, yield: 43%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08232287B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-7af1099dd3344c1d9f9ad543482cb904 |
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| Source note | uspto-grants-2012_07 |
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