Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(Dimethylamino)acetohydrazide | HCID 68319 | — |
| Reactant | ethoxy[3-(4fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride | HCID 22479739 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178483327 | HCID 178483327 | 92.1% |
Reaction Steps
To a solution of ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride (200 mg, 0.62 mmol), N-amino-2-(dimethylamino)acetamide (147.5 mg, 0.95 mmol), and molecular sieves in ethanol was added triethylamine (0.25 mL, 1.86 mmol). The reaction was allowed to stir under a nitrogen atmosphere at 75° C. overnight. The reaction was filtered using a fritted funnel and the filtrate was concentrated. This was purified by semi-preprative HPLC. The material was taken up in ethyl acetate and washed with aqueous sodium bicarbonate. This organic layer was dried with magnesium sulfate, filtered and concentrated to yield the title compound (192 mg, 23% yield). 1H NMR (CD3OD) δ 8.7 (s, 1H), 8.0-8.1 (m, 3H), 7.7 (d, 1H), 7.25 (t, 2H), 4.5 (s, 2H), 3.0 (s, 6H), ES-MS (m/z) 337 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06897231B2 |
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| Source dataset | uspto-grants-2005_05 |
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| ORD ID | ord-8c92fd755a25443d875a39b4c48863cb |
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| Source note | uspto-grants-2005_05 |
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