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Boron tribromide → 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxy-5-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 2095060
Notes
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Reaction equation

HRID 2095060 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:32][CH3:33])[CH:31]=1)[CH2:6][N:7]1[C:11]([CH3:13])([CH3:12])[C:10](=[O:14])[N:9]([C:15]2[CH:16]=[N:17][N:18]([CH2:20][C:21]3[C:22]([CH3:27])=[N:23][O:24][C:25]=3[CH3:26])[CH:19]=2)[C:8]1=[O:28].B(Br)(Br)Br>ClCCl>[CH3:27][C:22]1[C:21]([CH2:20][N:18]2[CH:19]=[C:15]([N:9]3[C:10](=[O:14])[C:11]([CH3:13])([CH3:12])[N:7]([CH2:6][C:5]4[CH:29]=[C:30]([O:32][CH3:33])[CH:31]=[C:3]([OH:2])[CH:4]=4)[C:8]3=[O:28])[CH:16]=[N:17]2)=[C:25]([CH3:26])[O:24][N:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 533751511-(3,5-dimethoxybenzyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 533736383-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxy-5-methoxybenzyl)-5,5-dimethylimidazolidine-2,4-dioneYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-(3,5-dimethoxybenzyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-5,5-dimethylimidazolidine-2,4-dione (Example 12-18) (114 mg, 0.252 mmol) was dissolved in dichloromethane (1 mL). The mixture was cooled down to −78° C. and boron tribromide (1.0 M solution in dichloromethane, 1.25 mL) was added dropwise. After complete addition, the mixture was allowed to warm to room temperature and stirring continued for 3 hours. The mixture was quenched with water and the organic phase was separated, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The residue was suspended in methanol (1 mL) and purified by reverse phase HPLC (25 minute gradient: acetonitrile/water). Yield 47% (45 mg), white solid. 1H NMR (DMSO-d6, 400 MHz): s, 6H), 2.16 (s, 3H), 2.42 (s, 3H), 3.67 (s, 3H), 4.43 (s, 2H), 5.20 (s, 2H), 6.22 (t, J=2.4 Hz, 1H), 6.39 (m, 2H), 7.83 (d, J=0.4 Hz, 1H), 8.21 (s, 1H), 9.40 (br s, 1H). Mp. 72-74° C. MS 440 (MH+). The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.02 μM.

Workup

  1. additionAfter complete addition
  2. temperatureto warm to room temperature
  3. customThe mixture was quenched with water
  4. customthe organic phase was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. custompurified by reverse phase HPLC (25 minute gradient: acetonitrile/water)

Sources & evidence

ORD record
ord-c8ed953b85104109b1a6968c02344c66
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08445692B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes