Potassium Carbonate → HCID 68349541, compound
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.Cl.[NH2:16][C@H:17]([CH3:30])[C:18]([C:21]1[O:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=1)([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:16][C@H:17]([CH3:30])[C:18]([C:21]3[O:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=3)([CH3:20])[CH3:19])=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (200 mg, 0.729 mmol) in DMF (15 mL) was added (R)-methyl 2-(3-amino-2-methylbutan-2-yl)oxazole-4-carboxylate hydrochloride (217 mg, 0.874 mmol) and potassium carbonate (302 mg, 2.186 mmol) at RT and the reaction mixture was allowed to stir at 50° C. for 52 h. It was then quenched with water (150 ml) and extracted with EtOAc (3×100 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. Crude product was purified by combiflash (12 g silica column, 60% EtOAc: Pet-Ether) to get desired product as yellow solid (85 mg, 25.9%). 1H NMR (400 MHz, DMSO) δ ppm: 1.23-1.25 (d, J=8.0 Hz, 3H), 1.42-1.44 (d, J=8.0 Hz, 6H), 3.79 (s, 3H), 4.61-4.62 (d, J=4.0 Hz, 1H), 7.09-7.10 (d, J=4.0 Hz, 1H), 7.892-7.896 (d, J=1.6 Hz, 1H), 8.22 (s, 1H), 8.75 (s, 1H), 10.91-10.95 (t, J=16.0 Hz, 1H). LC retention time: 1.680 min (analytical HPLC Method P).
Workup
- customIt was then quenched with water (150 ml)
- extractionextracted with EtOAc (3×100 mL)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- concentrationconcentrated under vacuum
- customCrude product was purified by combiflash (12 g silica column, 60% EtOAc: Pet-Ether)
Sources & evidence
- ORD record
- ord-3df077540dcf423bbc7275836a97883f
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221826B2
Reaction notes
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