Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Hydrazine hydrate (1:1) | HCID 24654 | — |
| Reactant | Dimethylformamide dimethyl acetal | HCID 78373 | — |
| Reactant | 4-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamide | HCID 59250027 | — |
| Product | HCID 178477985 | HCID 178477985 | 43.6% |
Reaction Steps
A mixture of 4-(2,4-dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamide (23 mg, 0.06 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.8 mL, 6 mol) was irradiated in the microwave at 160° C. (300 watts) for 30 minutes. The reaction was concentrated in vacuo. The residue dissolved in acetic acid (1.0 mL, 0.18 mol) and hydrazine hydrate (30 mg, 0.7 mmol) and subjected to microwave irradiation at 120° C. (300 watts) for 15 minutes. The solvent was removed in vacuo, the residue was diluted with water (1 mL), the precipitate was collected, washed with water (1 mL) and dried to afford the title compound (10 mg, 40%). LCMS: (FA) ES+, 382. 1H NMR (400 MHz, d6-DMSO) δ: 13.9 (s, 1H), 8.42 (s, 1H), 7.63 (d, 1H), 7.44-7.42 (m, 2H), 3.73-3.70 (m, 4H), 3.44-3.42 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08440664B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-6f8917ace2574e119f3133ee1adf1cbd |
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| Source note | uspto-grants-2013_05 |
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