Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 68107370 | HCID 68107370 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 51036181 | HCID 51036181 | 77.1% |
Reaction Steps
7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-(dimethylaminomethyl)-2,3-dihydrobenzofuran-4-carboxylic acid 29j (30 mg, 0.06 mmol) was dissolved in 10 mL of dichloromethane followed by the addition of 1-methyl-piperidyl-4-yl-amine (7 mg, 0.06 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (20 mg, 0.06 mmol) and diisopropylethylamine (24 mg, 0.18 mmol). The reaction solution was stirred for 2 hours. The resulting solution was added with 10 mL of saturated sodium chloride solution and extracted with dichloromethane (10 mL×3). The combined organic phase was washed with water (10 mL) and saturated sodium chloride solution (10 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-(dimethylaminomethyl)-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 29 (27 mg, yield: 77.1%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691822B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-a3afb8f030544595be1934d0ca3b73f2 |
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| Source note | uspto-grants-2014_04 |
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