1,3-Dibromo-5,5-dimethylhydantoin → 7-Bromo-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine
Reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]3[N:16]([CH:17]=2)[N:15]=[CH:14][N:13]=[C:12]3[NH2:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:19]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[Br:19][C:17]1[N:16]2[C:11]([C:12]([NH2:18])=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[CH2:8][CH2:7][CH2:6][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the compound (257 mg, 1.05 mmol) prepared in Example 12 in DMF (8 mL) at −78° C. was added 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (150 mg, 0.52 mmol) portion wise over a period of 5 minutes. The reaction was stirred for 30 minutes and was allowed to warm to room temperature, and stirred overnight. DMF was removed under vacuum, and the crude solid was extracted with DCM/sodium hydroxide (1N) solution. The organic layer was dried, concentrated, and the crude product was purified by prep HPLC. The pure fractions were concentrated, extracted with saturated sodium bicarbonated/DCM, and the organic layer was dried sodium sulfate, filtered and concentrated to obtain the title compound (135 mg) having the following physical data.