Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Methoxybenzylamine | HCID 75452 | — |
| Reactant | HCID 18446570 | HCID 18446570 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 18446542 | HCID 18446542 | 94% |
Reaction Steps
A mixture of 4-chloro-2-phenyl-thiazolo[4,5-c]pyridine-7-carbonitrile 47 (54.2 mg, 0.2 mmol) and potassium carbonate (66 mg, 0.48 mmol) in NMP (1 mL) was treated with 4-methoxybenzylamine (32.5 μL, 2.4 mmol) and the mixture stirred at 130° C. for 8 hours. Silica gel column chromatography (eluent: dichloromethane and ethyl acetate (10 to 1)) afforded 48 as a pale yellow solid (70 mg). 1H NMR (400 MHz, d6-DMSO) δ: 3.71 (s, 3H), 4.72 (d, J=5.9 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.4 Hz, 2H), 7.60 (m, 3H), 8.15 (m, 2H), 8.47 (s, 1H), 8.84 (t, J=6.1 Hz, 1H). MS (EI) m/z (M+H+) 373.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07635695B2 |
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| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-4825a4859245488c84e4a3486829d057 |
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| Source note | uspto-grants-2009_12 |
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