Cyclohexane, (bromomethyl)- → HCID 57944902, compound

HRID 1770566Notes

Reaction equation

HRID 1770566 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N:13]3[C:17](=[O:18])[CH2:16][NH:15][C:14]3=[O:19])[CH:10]=[N:9]2)=[C:5]([CH3:20])[O:4][N:3]=1.Br[CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[CH:23]1([CH2:22][N:15]2[CH2:16][C:17](=[O:18])[N:13]([C:11]3[CH:10]=[N:9][N:8]([CH2:7][C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:20])[CH:12]=3)[C:14]2=[O:19])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 137636Cyclohexane, (bromomethyl)-HCID 574224243-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione

Product 1

HCID 57944902HCID 57944902, compoundYield 20%

Procedure

Prepared as in example 10-52 from 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (example 10-1) and bromomethylcyclohexane. Yield: 20%. 1H NMR (DMSO-d6, 400 MHz): δ0.88 (q, J=10.4 Hz, 2H), 1.09-1.19 (m, 3H), 1.58-1.65 (m, 6H), 2.12 (s, 3H), 2.38 (s, 3H), 3.13 (d, J=7.2 Hz, 2H), 4.06 (s, 2H), 5.17 (s, 2H), 7.75 (s, 1H), 8.14 (s, 1H). MS M+H calculated 372.2. Found 372.1. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.28 μM.

Sources & evidence

ORD record
ord-9aff6b5240364e9e9048858e0ccf5b9e
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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