5-Fluoro-1,3-thiazol-2-amine hydrochloride → (E)-3-cyclopentyl-2-(6-ethylsulfanylpyridin-3-yl)-N-(5-fluorothiazol-2-yl)acrylamide

HRID 855548Notes

Reaction equation

HRID 855548 reaction equation
[CH:1]1(/[CH:6]=[C:7](\[C:11]2[CH:12]=[N:13][C:14]([S:17][CH2:18][CH3:19])=[CH:15][CH:16]=2)/[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[F:21][C:22]1[S:26][C:25]([NH2:27])=[N:24][CH:23]=1>>[CH:1]1(/[CH:6]=[C:7](\[C:11]2[CH:12]=[N:13][C:14]([S:17][CH2:18][CH3:19])=[CH:15][CH:16]=2)/[C:8]([NH:27][C:25]2[S:26][C:22]([F:21])=[CH:23][N:24]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 118589315-Fluoro-1,3-thiazol-2-amine hydrochlorideHCID 58935725(E)-3-cyclopentyl-2-(6-ethylsulfanylpyridin-3-yl)acrylic acid

Product 1

HCID 86594356(E)-3-cyclopentyl-2-(6-ethylsulfanylpyridin-3-yl)-N-(5-fluorothiazol-2-yl)acrylamide

Procedure

Condensation of (E)-3-cyclopentyl-2-(6-ethylsulfanylpyridin-3-yl)acrylic acid (Preparation 4, 215 mg, 0.78 mmol) with 5-fluorothiazol-2-ylamine hydrochloride (Preparation 21, 240 mg, 1.55 mmol), by the protocol described in EXAMPLE 5, yielded (E)-3-cyclopentyl-2-(6-ethylsulfanylpyridin-3-yl)-N-(5-fluorothiazol-2-yl)acrylamide: m/z (ES+)=378.2 [M+H]+. Oxidation of this thioether (22 mg, 60 μmol), by the protocol described in EXAMPLE 55, gave the title compound: RTA=3.50 min; m/z (ES+)=394.2 [M+H]+.

Sources & evidence

ORD record
ord-ba2f2e17d1684a9b94123c55c341c2cd
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

Loading…