1,3-Dibromo-5,5-dimethylhydantoin → HCID 57955185, compound

HRID 73705Notes

Reaction equation

HRID 73705 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH2:11][N:12]1[CH2:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:19].[Br:20]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)Cl>[Br:20][C:3]1[C:2]([CH3:1])=[C:10]([CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:9]2[C:4]=1[C:5]([NH2:19])=[N:6][CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 579552106-Methyl-7-(1,4-oxazepan-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 57955185HCID 57955185, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of chloroform (20 mL) and 6-methyl-7-(1,4-oxazepan-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (650 mg, 2.49 mmol), at −40° C., was added 1,3-dibromo-5,5-dimethylhydantoin (356 mg, 1.24 mmol). The mixture was allowed to stir for 10 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 500 mg (59%) of the desired product. 1H-NMR (DMSO-d6) δ 7.82 (s, 1H), 3.91 (s, 2H), 3.62 (t, J=5.4 Hz, 2H), 3.55-3.53 (m, 2H), 2.61-2.56 (m, 4H), 2.15 (s, 3H), 1.77-1.72 (m, 2H); MS [M+H]+=339.9, 341.9; LCMS RT=1.09.

Workup

  1. customThe mixture was partitioned between ethyl acetate (200 mL) and saturated aqueous Na2CO3 solution (150 mL)
  2. customThe layers were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c885f83978074532a86dbf78633a7953
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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