Hydrochloric Acid → 1217341-48-4

HRID 658758Notes

Reaction equation

[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:35]=[CH:36][CH:37]=1)[CH2:12][N:13]1[C:17]([CH3:19])([CH3:18])[C:16](=[O:20])[N:15]([C:21]2[CH:22]=[N:23][N:24]([CH2:26][C:27]3[C:28]([CH3:33])=[N:29][O:30][C:31]=3[CH3:32])[CH:25]=2)[C:14]1=[O:34])(C(C)(C)C)(C)C.Cl>CO>[CH3:33][C:28]1[C:27]([CH2:26][N:24]2[CH:25]=[C:21]([N:15]3[C:16](=[O:20])[C:17]([CH3:19])([CH3:18])[N:13]([CH2:12][C:11]4[CH:35]=[CH:36][CH:37]=[C:9]([OH:8])[CH:10]=4)[C:14]3=[O:34])[CH:22]=[N:23]2)=[C:31]([CH3:32])[O:30][N:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1-(3-(tert-butyldimethylsilyloxy)benzyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-5,5-dimethylimidazolidine-2,4-dione (Example 12-1a) (2.00 g, 3.82 mmol) was dissolved in methanol (200 mL) and treated with HCl (2.0 M solution in diethyl ether, 10 equivalents). The solution was stirred for 16 hours at 50° C. then allowed to cool down to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in ethanol and recrystallized at 4° C. to give 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)-5,5-dimethylimidazolidine-2,4-dione (1.50 g, 3.67 mmol, 96%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): 1.31 (s, 6H), 2.16 (s, 3H), 2.42 (s, 3H), 4.47 (s, 2H), 5.20 (s, 2H), 6.65 (ddd, J=0.8, 2.4, 8 Hz, 1H), 6.79 (m, 2H), 7.11 (t, J=8 Hz, 1H), 7.83 (d, J=0.8 Hz, 1H), 8.21 (d, J=0.8 Hz, 1H), 9.36 (s, H). MS 410 (MH+). The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.05 μM

Workup

temperatureto cool down to room temperature
customthe solvent was removed under reduced pressure
dissolutionThe residue was dissolved in ethanol
customrecrystallized at 4° C.

Sources & evidence

ORD record: ord-ba18cb6e5a514823b94a6d200bd7b7ea
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076491B2

Reaction notes

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