1,3-Dibromo-5,5-dimethylhydantoin → HCID 57955300, compound

HRID 73677Notes

Reaction equation

HRID 73677 reaction equation
C1COCC1.[NH2:6][C:7]1[C:12]2=[C:13]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:30]=4[F:39])=[O:27])=[C:21]([F:40])[CH:20]=3)[C:14]([CH2:16][O:17][CH3:18])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1.[Br:41]N1C(C)(C)C(=O)N(Br)C1=O.[O-]S([O-])=O.[Na+].[Na+]>CCOC(C)=O>[NH2:6][C:7]1[C:12]2=[C:13]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[CH:31][C:30]=4[F:39])=[O:27])=[C:21]([F:40])[CH:20]=3)[C:14]([CH2:16][O:17][CH3:18])=[C:15]([Br:41])[N:11]2[N:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 57758195HCID 57758195, compound

Product 1

HCID 57955300HCID 57955300, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of THF (500 mL) was added 1-{4-[4-amino-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]-2-fluorophenyl}-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea (2.29 g, 4.65 mmol). The solution was cooled to −40° C. and then 1,3-dibromo-5,5-dimethylhydantoin (665 mg, 2.33 mmol) was added in two batches 20 min apart. The reaction was stirred at −40° C. for 1 h and then allowed to warm to rt over the following 2 h. Aq saturated Na2SO3 was added to the reaction followed by EtOAc. The layers were separated and the aqueous layer was back extracted with EtOAc. The organic layer was washed with 1 N NaOH and water, dried (Na2SO4), filtered and evaporated to yield 2.83 g crude (107%) of the desired product. MS [M+H]+=571; LCMS RT=3.54.

Workup

  1. temperatureto warm to rt over the following 2 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was back extracted with EtOAc
  4. washThe organic layer was washed with 1 N NaOH and water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-48137c0dc47a498eb3bcfda5df59c03b
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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