1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529949, compound

HRID 1972741Notes

Reaction equation

HRID 1972741 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[N:12]=[C:13]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)[S:14][CH:15]=3)[N:6]2[N:5]=[CH:4][N:3]=1.[Br:29]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C.CC(O)=O>[NH2:1][C:2]1[C:7]2=[C:8]([Br:29])[CH:9]=[C:10]([C:11]3[N:12]=[C:13]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)[S:14][CH:15]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 58529978HCID 58529978, compound

Product 1

HCID 58529949HCID 58529949, compoundYield 109.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (−20° C.) solution of tert-butyl 4-[4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (914 mg. 2.28 mmol) in DMF (12.6 mL) and AcOH (5 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (326 mg, 1.14 mmol) in 3 portions over 10 minutes. The mixture was stirred at 0° C. for 3 h. The reaction was quenched with the addition 5% aqueous K2CO3 (50 mL) and was allowed to warm to rt. The mixture was extracted with ethyl acetate (3×50 mL). The combined organics were washed with brine, dried (Na2SO4) and evaporated. The crude material was purified by ISCO® chromatography using a gradient of 50% to 75% ethyl acetate in hexanes to afford 596 mg (54%) of the desired product. ES-MS m/z 480.85 [M+H]+, HPLC RT (min) 3.45.

Workup

  1. customThe reaction was quenched with the addition 5% aqueous K2CO3 (50 mL)
  2. temperatureto warm to rt
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude material was purified by ISCO® chromatography

Sources & evidence

ORD record
ord-7309a98d23c14e82bee54a90bba21eb2
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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