Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1) | HCID 3017050 | — |
| Reactant | HCID 135729082 | HCID 135729082 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 58691336 | HCID 58691336 | — |
Reaction Steps
A mixture of N-(4-(6-(2-hydroxy-4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)-acetamide (89 mg, 0.2 mmol, prepared as described in WO04014871), 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (56 mg, 0.3 mmol, Aldrich), sodium carbonate (62 mg, 0.6 mmol, Aldrich), sodium iodide (45 mg, 0.3 mmol) and acetone (1 mL) was heated in a microwave synthesizer at 150° C. for 40 min. The reaction mixture diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (10% MeOH/CH2Cl2) to give the title compound as an amorphous solid. MS (ESI, pos. ion.) m/z: 558 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07301022B2 |
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| Source dataset | uspto-grants-2007_11 |
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| ORD ID | ord-73fb5bf3c6c2471f91040e437fee93e5 |
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| Source note | uspto-grants-2007_11 |
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