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

HRID 1487318Notes

Reaction equation

HRID 1487318 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]([CH3:21])[CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[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]([CH3:21])[CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[CH2:17]3)=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68350278(3S,4S)-benzyl 3-amino-4-methylpyrrolidine-1-carboxylateHCID 899954732-Bromo-8-chloro-imidazo[1,2-b]pyridazine-7-carboxamide

Product 1

HCID 89995493(3S,4S)-Benzyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-methylpyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-8-chloroimidazo[1,2-b]pyridazine-7-carboxamide (2.198 g, 7.98 mmol), (3S,4S)-benzyl 3-amino-4-methylpyrrolidine-1-carboxylate (2.15 g, 9.18 mmol) and Hunig's Base (4.18 ml, 23.94 mmol) in DMF (7.9 ml) in a reaction vial was stirred at 90° C. for 2 h. After cooling to room temperature, the reaction solution was added slowly to a stirred ice-water resulting in a light tan precipitate. The suspension was stirred for 30 min. (3S,4S)-Benzyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-methylpyrrolidine-1-carboxylate (3.78 g, 7.98 mmol, 100% yield) was collected as a light tan solid via filtration. ESI-MS (analytical LCMS Method A): m/z 473, 475 ([M+H]+). HPLC (analytical HPLC Method A) Rt: 3.808 min.

Sources & evidence

ORD record
ord-5188d3f52c6b4d4bb4cd219577d753ec
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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