1,3-Dibromo-5,5-dimethylhydantoin → HCID 59232168, compound

HRID 1091498Notes

Reaction equation

HRID 1091498 reaction equation
[C:1]([C:4]1[N:12]2[C:7]([C:8]([NH2:13])=[N:9][CH:10]=[N:11]2)=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=3[F:34])=[O:22])=[CH:16][CH:15]=2)[CH:5]=1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[Br:56]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[Br:56][CH2:2][C:1]([C:4]1[N:12]2[C:7]([C:8]([NH2:13])=[N:9][CH:10]=[N:11]2)=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=3[F:34])=[O:22])=[CH:16][CH:15]=2)[CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 65367Trimethylsilyl triflateHCID 81531DiisopropylethylamineHCID 59232118HCID 59232118, compound

Product 1

HCID 59232168HCID 59232168, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of Example 100 in THF (5 mL) was cooled to −78° C. and treated with diisopropylethyl amine (0.424 mL, 2.57 mmol) followed by trimethylsilyltriflate (0.421 mL, 2.177 mmol). The reaction was allowed to warm to rt over 30 min, then cooled again to −78° C. and treated with 1,3-dibromo-5,5-dimethylhydantoin (62 mg, 0.218 mmol). The reaction was allowed to stir for 1 h at −78 C, then warmed to rt and quenched with methanol (200 uL) and diluted with ethyl acetate and 1N sodium sulfite solution. The organic layer was separated, washed with 1 N bisulfate buffer (pH 2), dried with sodium sulfate and passed thru a silica plug. Evaporation of the solvent gave a yellow solid which was triturated with Et2O:hexanes (1:1) to provide the title compound as a yellow solid (154 mg, 70% Yield). 1H-NMR (DMSO-d6) δ 9.18 (s, 1H), 8.45 to 8.48 (m, 1H), 8.02 (s, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 7.27 (s, 1H), 7.20 to 7.37 (m, 4H), 4.77 (s, 2H). MS [M+H]+=551.2; LCMS RT=3.63.

Workup

  1. temperaturecooled again to −78° C.
  2. temperaturewarmed to rt
  3. customquenched with methanol (200 uL)
  4. additiondiluted with ethyl acetate and 1N sodium sulfite solution
  5. customThe organic layer was separated
  6. washwashed with 1 N bisulfate buffer (pH 2)
  7. dry with materialdried with sodium sulfate
  8. customEvaporation of the solvent
  9. customgave a yellow solid which
  10. customwas triturated with Et2O:hexanes (1:1)

Sources & evidence

ORD record
ord-a5be6fe377e946629b0e81fa89c9ea04
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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