Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 68358955 | HCID 68358955 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68291788 | HCID 68291788 | 57.3% |
Reaction Steps
To a stirred solution of (1S,3R)-3-(6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)-1,2,2-trimethylcyclopentanecarboxylic acid (182 mg, 0.445 mmol) in DMF (3.0 ml), were added Hunig's base (582 μl, 3.34 mmol) and HATU (254 mg, 0.667 mmol). After 15 minutes, ammonium chloride (119 mg, 2.223 mmol) was added. The reaction was heated at 75° C. for 24 hrs. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The solution was washed successively with water, (sat.) ammonium chloride and (sat.) sodium chloride. The ethyl acetate extract was dried with sodium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (104 mg, 0.255 mmol, 57.3% yield) as a white solid. LC/MS found [M+H]+=409.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921368B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-b4a213210fc4401d992daf3adccbe49d |
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| Source note | uspto-grants-2014_12 |
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