Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 3-Methoxybenzoic Acid | HCID 11461 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | HCID 54328958 | HCID 54328958 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 9912198 | HCID 9912198 | — |
Reaction Steps
A mixture of 4-{3-[(S)-1,2,3,4-tetrahydro-isoquinolin-3-yl-methyl]-3H-imidazol-4-yl-methyl}-benzonitrile (0.16 g, 0.487 mmol), 3-methoxybenzoic acid (0.074 g, 0.487 mmol), 1-hydroxybenzotriazole (0.075 g, 0.487 mmol), EDC (0.093 g, 0.487 mmol) and N-methylmorpholine (0.2 ml, 1.95 mmol) in 5 ml DMF was stirred for 18 hr at 25° C. The solvent was removed in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The ethyl acetate layer was dried with saturated sodium chloride and magnesium sulfate. Evaporation in vacuo of the ethyl acetate layer yielded the crude product. Purification was done on silica gel using methylene chloride:methanol:amonia hydroxide 98:2:0.2 and yielded the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05932590 |
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| Source dataset | uspto-grants-1999_08 |
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| ORD ID | ord-582b6081bc7e4b3e9c7f8a40d5853c9a |
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| Source note | uspto-grants-1999_08 |
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