Diisopropylethylamine → (3S,4S)-Benzyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-ethylpyrrolidine-1-carboxylate

HRID 1487325Notes

Reaction equation

[Br:1][C:2]1[N: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[C@@H:20]([CH2:21][CH3:22])[CH2:19][N:18]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:17]1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[C:9]([NH:15][C@H:16]3[C@@H:20]([CH2:21][CH3:22])[CH2:19][N:18]([C:23]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:24])[CH2:17]3)=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-bromo-8-chloroimidazo[1,2-b]pyridazine-7-carboxamide (0.940 g, 3.41 mmol), (3S,4S)-benzyl 3-amino-4-ethylpyrrolidine-1-carboxylate (1.017 g, 4.09 mmol) and Hunig's Base (1.788 ml, 10.24 mmol) in DMF (3.0 ml) in a reaction vial was stirred at 90° C. for 2 h. The reaction solution was added slowly to a stirred ice-water resulting in a light tan precipitate. The suspension was stirred for 30 min at 0° C. After filtration, (3S,4S)-benzyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-ethylpyrrolidine-1-carboxylate was collected as a light tan solid (1.716 g, 3.52 mmol, 100% yield). ESI-MS (analytical LCMS Method A): m/z 489.1, 487.1 ([M+H]+).

Workup

filtrationAfter filtration, (3S,4S)-benzyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-ethylpyrrolidine-1-carboxylate

Sources & evidence

ORD record: ord-4f585862ae5c482eacb432fc79af68d9
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428511B2

Reaction notes

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