1,3-Dibromo-5,5-dimethylhydantoin → HCID 59232020, compound

HRID 1099271Notes

Reaction equation

HRID 1099271 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.[Br:18]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Br:18])[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 59232114HCID 59232114, compound

Product 1

HCID 59232020HCID 59232020, compoundYield 154.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of butyl 4-aminopyrrolo[2,1-f][1,2,4]triazine-7-carboxylate (225.0 mg, 0.96 mmol) in DMF (7.5 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (137.3 mg, 0.48 mmol) in two portions. The solution was stirred for 4 days and then quenched by addition of saturated aqueous sodium sulfate solution (20 mL) and water (20 mL). The solid was filtered, washed with water and air-dried. The crude material was purified by HPLC using a gradient of 30-80% of MeCN in water to afford 232.0 mg (77%) of the title compound as an off-white solid. 1H-NMR (DMSO-d6) δ 8.42 (bs, 1 H), 8.03 (s, 1 H), 7.35 (s, 1 H), 7.03 (bs, 1 H), 4.23 (t, J=6.4 Hz, 2 H), 1.69-1.62 (m, 2 H), 1.46-1.36 (m, 2 H), 0.92 (t, J=7.3, 3H); MS [M+H]+=313.0; LCMS RT=2.83 min.

Workup

  1. customquenched by addition of saturated aqueous sodium sulfate solution (20 mL) and water (20 mL)
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customair-dried
  5. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-3b03de2fc66c49cba0ca44462ec1d81a
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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