Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | HCID 58442440 | HCID 58442440 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 58442435 | HCID 58442435 | 64.3% |
Reaction Steps
A mixture of 2-chloro-N-(4-mesitylthiazol-2-yl)isonicotinamide (500.0 mg, 1.4 mmol, 1.0 equiv) and morpholine (1.5 mL, 16.8 mmol, 12 equiv) in methylpyrrolidone (15.0 mL) was stirred at 150° C. for 16 h. The mixture was poured into icy H2O (20.0 mL), and the resultant solids were filtered to provide N-(4-mesitylthiazol-2-yl)-2-morpholinoisonicotinamide (358.6 mg, 0.90 mmol) as yellow solids in 63% yield: 1H NMR (DMSO-d6, 500 MHz) δ 8.30 (d, J=5.1 Hz, 2 H), 7.50 (s, 1 H), 7.22 (d, J=5.1 Hz, 2 H), 7.10 (s, 1H), 6.92 (s, 2 H), 3.70-3.73 (m, 4 H), 3.53-3.55 (m, 4 H), 2.26 (s, 3 H), 2.05 (s, 6H); ESI-MS: m/z 409.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08999983B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-7c6f81376d334ab68579245ff10a70de |
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| Source note | uspto-grants-2015_04 |
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