1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529694, compound

HRID 1972746Notes

Reaction equation

HRID 1972746 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH2:11][CH:12]3[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]3)[N:6]2[N:5]=[CH:4][N:3]=1.[Br:23]N1C(C)(C)C(=O)N(Br)C1=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(O)=O>[NH2:1][C:2]1[C:7]2=[C:8]([Br:23])[CH:9]=[C:10]([CH2:11][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 11430Potassium CarbonateHCID 58529825HCID 58529825, compound

Product 1

HCID 58529694HCID 58529694, compoundYield 192.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To a cooled (−20° C.) solution of tert-butyl 3-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]azetidine-1-carboxylate (325 mg, 1.07 mmol) in DMF (5 mL) and AcOH (1 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (153 mg, 0.54 mmol) in 3 portions over 10 min. The mixture was stirred at −20° C. for 3 h. Aqueous K2CO3 (5%, 20 mL) was added and the mixture was allowed to warm to rt. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to provide 397 mg (97%) of the desired product, which contained minor impurities. ES-MS m/z 382.08 [M+H]+, HPLC RT (min) 3.05.

Workup

  1. temperatureto warm to rt
  2. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-12461921e4264fd58d672c9f5243898c
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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