Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide | HCID 68291192 | — |
| Reactant | HCID 68350312 | HCID 68350312 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68350400 | HCID 68350400 | 87% |
Reaction Steps
A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 2, 0.4 g, 1.46 mmol) in DMF (2 mL), was added (3R,4S)-benzyl 3-amino-4-methoxypyrrolidine-1-carboxylate (enantiopure Intermediate 12, 0.40 g, 1.60 mmol) and N,N-diisopropylethylamine (0.3 mL, 3.1 mmol). The mixture was heated at 85° C. overnight. After cooling, the mixture was added water, stirred for 3 h, filtered, rinsed with water, and dried to give (3R,4S)-benzyl 3-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-4-methoxypyrrolidine-1-carboxylate (0.62 g, 87% yield) as a brown solid. MS (ES+) m/z: 487.1, 488.3 (M+H); LC retention time: 3.82 min (analytical HPLC Method).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08987268B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-9a7f23d0ab9b4296b5e5f29172f7b688 |
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| Source note | uspto-grants-2015_03 |
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