Acetic Acid → HCID 68291228, compound

HRID 877752Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[NH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][C@H:17]1[CH2:29][CH3:30].CC(O)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:15][C@@H:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:18][C@H:17]3[CH2:29][CH3:30])=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 2, 334 mg, 1.217 mmol) and (3R,4R)-tert-butyl 4-amino-3-ethylpiperidine-1-carboxylate (1.2 eq., Intermediate 8), AcOH (351 mg, 1.217 mmol) in DMF (3.0 ml) was added DIEA (1275 μl, 7.30 mmol). The reaction was heated at 90° C. for 5 hrs. The reaction was diluted with ethyl acetate (100 ml), and washed with water (3×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified via medium pressure chromatography (silica gel column, EtOAc/hexanes eluent, 0-100% gradient elution) to afford (3R,4R)-tert-butyl 4-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-3-ethylpiperidine-1-carboxylate (428.4 mg, 0.919 mmol, 75.0% yield) as a faint yellow solid. LCMS (Method K) m/z 468.2 ([M+H]+).

Workup

washwashed with water (3×100 ml)
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified via medium pressure chromatography (silica gel column, EtOAc/hexanes eluent, 0-100% gradient elution)

Sources & evidence

ORD record: ord-41d2037ecc234be4bbb70745c7e6ae56
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987268B2

Reaction notes

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