Ethyl 2-Isocyanato-4-Methylvalerate → HCID 57422476, compound

HRID 548155Notes

Reaction equation

HRID 548155 reaction equation
Cl.[CH3:2][C:3]1[C:7]([CH2:8][N:9]2[CH:13]=[C:12]([NH2:14])[CH:11]=[N:10]2)=[C:6]([CH3:15])[O:5][N:4]=1.[N:16]([CH:19]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:20](OCC)=[O:21])=[C:17]=[O:18]>>[CH3:2][C:3]1[C:7]([CH2:8][N:9]2[CH:13]=[C:12]([N:14]3[C:20](=[O:21])[CH:19]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:16][C:17]3=[O:18])[CH:11]=[N:10]2)=[C:6]([CH3:15])[O:5][N:4]=1

Participants

3

Reactant 2

HCID 522132Ethyl 2-Isocyanato-4-MethylvalerateHCID 574222641-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochloride

Product 1

HCID 57422476HCID 57422476, compoundYield 50%

Procedure

Prepared as in Example 10-41 from 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochloride (example 10-41a) and ethyl 2-isocyanato-4-methylpentanoate. Yield: 50%. 1H NMR (CDCl3, 400 MHz): δ 1.01-0.98 (m, 8H), 1.87-1.82 (m, 1H), 2.19 (s, 3H), 2.41 (s, 3H), 4.13-4.12 (t, 1H), (5.05 (s, 2H), 5.70 (bs, 1H), 7.90 (s, 1H), 8.05 (s, 1H). The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 1.0 μM.

Sources & evidence

ORD record
ord-9b6cead328e04d5c96d6ebf2e1b5bc2e
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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