1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529321, compound

HRID 1972881Notes

Reaction equation

HRID 1972881 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18]3[N:26]4[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]4)=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:28]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18]3[N:26]4[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]4)=[C:20]([Br:28])[CH:19]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 58529670HCID 58529670, compound

Product 1

HCID 58529321HCID 58529321, compoundYield 150%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 7-(4-amino-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (2.2 g, 6.1 mmol) in THF (30 mL) at −20° C. was added 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione (884 mg, 3 mmol) in four portions. The reaction mixture was allowed to stir at −20° C. for 2 h. The solvent was evaporated and the residue was purified by column chromatography (10-50% EtOAc/Hexane) to provide 2 g (72%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.9 (s, 1 H), 7.85 (d, 2 H), 7.2 (d, 2 H), 4.5 (s, 2 H), 3.5 (t, 2 H), 2.8 (t, 2 H), 1.4 (s, 9 H); ES-MS m/z 444.08 [M+H]+, HPLC RT (min) 3.24.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (10-50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-81e8e6ab236145748f3bfc5456c77257
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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