1,3-Dibromo-5,5-dimethylhydantoin → HCID 57955240, compound

HRID 73707Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:11].[Cl-].[CH2:13]=[N+:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[Br:20]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[Br:20][C:3]1[C:2]([CH3:1])=[C:10]([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:9]2[C:4]=1[C:5]([NH2:11])=[N:6][CH:7]=[N:8]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 6-methylpyrrolo[2,1-f][1,2,4]triazin-4-amine (350 mg, 2.36 mmol) in DMF (5 mL), was added 4-methylenemorpholin-4-ium chloride (Eur. J. Med. Chem. 1989, 24, 379-384) (750 mg, 2.84 mmol) at rt. The reaction was stirred for 17 hr, cooled to −78° C., and treated with 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (337 mg, 1.18 mmol). The reaction was allowed to stir for 30 minutes while warming to rt. The mixture was partitioned between ethyl acetate (200 mL) and saturated aqueous Na2CO3 solution (150 mL). The layers were separated and the organic phase was washed with brine, dried (Na2SO4), and concentrated to dryness. Trituration with acetonitrile afforded 300 mg (39%) of the desired product. 1H-NMR (DMSO-d6) δ 7.83 (s, 1H), 3.76 (s, 2H), 3.50-3.47 (m, 4H), 2.36-2.32 (m, 4H), 2.15 (s, 3H); MS [M+H]+=325.9, 327.9; LCMS RT=1.10.

Workup

stirringto stir for 30 minutes
temperaturewhile warming to rt
customThe mixture was partitioned between ethyl acetate (200 mL) and saturated aqueous Na2CO3 solution (150 mL)
customThe layers were separated
washthe organic phase was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-0333f0d5afd04e5b818499ebca679167
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829185B2

Reaction notes

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