Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | HCID 58236112 | HCID 58236112 | — |
| Catalyst | 2-Dimethylaminopyridine | HCID 21885 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89312411 | HCID 89312411 | 82.1% |
Reaction Steps
A suspension of 2-(3-pyridyl)thiazole-5-carbonyl chloride (4.6 g, 19.5 mmol) prepared according to WO 2009/149858) in methylene chloride (100 ml) was cooled to 0° C. and treated with triethyl amine (6.03 g, 58.4 mmol), dimethylamino pyridine (12 mg, 0.097 mmol) and then N-methoxymethanamine hydrochloride (2.9 g, 29.2 mmol). The mixture was allowed to warm up to ambient temperature and monitored by TLC and LC/MS. After completion, the reaction mixture was diluted with methylene chloride, washed with water, dried over magnesium sulfate, and the solvent removed by concentration in vacuo, to give 3.99 g (82%) of N-methoxy-N-methyl-2-(3-pyridyl)thiazole-5-carboxamide as a pale solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09060519B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-c057f0659ee54262b102c7d77f0ce486 |
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| Source note | uspto-grants-2015_06 |
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