Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,4-Dibromobutane | HCID 8056 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 86646904 | HCID 86646904 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86646903 | HCID 86646903 | 10% |
Reaction Steps
N-(2-{[7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-N,1-dimethyl-1H-imidazole-4-sulfonamide hydrochloride (98), 1,4-dibromobutane (49.9 mg, 0.231 mmol), and triethylamine (31.2 mg, 0.308 mmol) were dissolved in acetonitrile (3 ml) and stirred for 2 h at 130° C. in the microwave. Water and ethyl acetate were added and the organic phase was separated. After extraction of the aqueous phase with ethylacetate the combined organic layers were washed with saturated NaCl solution, dried over Na2SO4, and concentrated to afford a residue a residue that was purified by flash chromatography (silica gel, MeOH/CH2Cl2 5:95). The residue was transferred to an HCl salt and finally gave the product as a white solid (8.5 mg, 10%) after precipitation from diisopropylether.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08563617B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-df776ae9c7a74ff6b0b2762ce4b5b9d3 |
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| Source note | uspto-grants-2013_10 |
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