1,3-Dibromo-5,5-dimethylhydantoin → HCID 59232003, compound

HRID 1099264Notes

Reaction equation

[O:1]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]2[N:17]3[C:12]([C:13]([NH2:18])=[N:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.[Br:19]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)Cl>[Br:19][C:11]1[CH:10]=[C:9]([CH2:8][N:4]2[CH2:5][CH2:6][CH2:7][O:1][CH2:2][CH2:3]2)[N:17]2[C:12]=1[C:13]([NH2:18])=[N:14][CH:15]=[N:16]2

Participants

Conditions

Temperature: -25 °C

Procedure

7-(1,4-oxazepan-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (1.90 g, 7.68 mmol) was suspended in chloroform (76 mL). The solution was cooled to −20 to −30° C. 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione ( 989 g, 3.46 mmol) was added. The reaction was maintained at −20° C. for 20 minutes then warmed to room temperature. An LC taken at that time showed the reaction to be essentially complete. The reaction was then quenched by the addition of saturated aqueous sodium sulfite. The resultant slurry was partitioned between ethyl acetate (300 mL) and saturated bicarbonate (100 mL). The organic layer was washed (3×100 mL) with bicarb then dried with Na2SO4 and concentrated under vacuum.

Workup

temperatureThe reaction was maintained at −20° C. for 20 minutes
temperaturethen warmed to room temperature
customthe reaction
customThe reaction was then quenched by the addition of saturated aqueous sodium sulfite
customThe resultant slurry was partitioned between ethyl acetate (300 mL) and saturated bicarbonate (100 mL)
washThe organic layer was washed (3×100 mL) with bicarb
dry with materialthen dried with Na2SO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-da9d0f12bfbb48449369ee1d16858625
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143393B2

Reaction notes

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