Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | N-((1R*,2R)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride | HCID 68451909 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 68447707 | HCID 68447707 | — |
Reaction Steps
The compound (30 mg) obtained in Example 23 was suspended in methylene chloride (20 mL), and triethylamine (260 μl) was added, followed by stirring at room temperature for 15 minutes. Acetic acid (179 μl) and acetone (920 μl) were added to the reaction mixture, and the resultant mixture was stirred at room temperature for 2 minutes. Sodium triacetoxyborohydride (796 mg) was added to the reaction mixture to stir them at room temperature for 5 hours. 1N aqueous sodium hydroxide (10 mL) was added to the reaction mixture for partitioning the mixture. The resultant organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give a colorless foamy substance. This product was dissolved in methylene chloride, and 1N HCl in ethanol (1 mL) was added. The solution was concentrated under reduced pressure to give the title compound (205 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07576135B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-9ee78d318ce34de28fa42fc2c2cd8091 |
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| Source note | uspto-grants-2009_08 |
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