2-Bromoethyl methyl ether → HCID 57422439, compound

HRID 658685Notes

Reaction equation

HRID 658685 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][N:15]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:26])[C:14]3=[O:27])[CH:10]=[N:9]2)=[C:5]([CH3:28])[O:4][N:3]=1.[CH3:29][O:30][CH2:31][CH2:32]Br>>[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][N:15]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH2:32][CH2:31][O:30][CH3:29])[C:14]3=[O:27])[CH:10]=[N:9]2)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 57422432HCID 57422432, compound

Product 1

HCID 57422439HCID 57422439, compoundYield 19%

Procedure

Prepared as in example 10-5 from 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(2-hydroxybenzyl)imidazolidine-2,4-dione (example 10-11) and 2-bromoethyl methyl ether. Yield 19%. 1H NMR (DMSO, 400 MHz): δ2.11 (s, 3H), 2.08 (s, 3H), 3.25 (s, 3H), 3.64 (t, J=3.6, 2H), 4.00 (s, 2H), 4.11 (t, J=3.2, 2H), 4.27 (s, 2H), 5.17 (s, 2H), 6.90 (m, 1H), 7.00 (m, 1H), 7.26 (m, 2H), 7.76 (s, 1H), 8.15 (s, 1H). The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.1 uM.

Sources & evidence

ORD record
ord-735a8bf00ee04fd5b79d04e277e8a8f9
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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