2-Amino-thiazole-5-carboxylic acid ethyl ester → HCID 86594355, compound

HRID 855546Notes

Reaction equation

HRID 855546 reaction equation
[CH:1]1(/[CH:6]=[C:7](\[C:11]2[CH:12]=[N:13][C:14]([S:17][CH:18]3[CH2:20][CH2:19]3)=[CH:15][CH:16]=2)/[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:21][C:22]1[S:23][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:26]=1>>[CH:1]1([CH:6]=[C:7]([C:11]2[CH:12]=[N:13][C:14]([S:17][CH:18]3[CH2:20][CH2:19]3)=[CH:15][CH:16]=2)[C:8]([NH:21][C:22]2[S:23][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:26]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 3146282-Amino-thiazole-5-carboxylic acid ethyl esterHCID 58935715HCID 58935715, compound

Product 1

HCID 86594355HCID 86594355, compound

Procedure

(E)-3-Cyclopentyl-2-(6-cyclopropylsulfanylpyridin-3-yl)acrylic acid (Preparation 15, 250 mg, 0.86 mmol) was condensed with ethyl 2-aminothiazole-5-carboxylate (297 mg, 1.73 mmol), using the method described in EXAMPLE 12, to furnish ethyl 2-[3-cyclopentyl-2-(6-cyclopropylsulfanylpyridin-3-yl)acryloylamino]thiazole-5-carboxylate: m/z (ES+)=444.3 [M+H]+. This ester was saponified, employing a procedure similar to that described in Step 3 of Preparation 16, to give 2-[3-cyclopentyl-2-(6-cyclopropylsulfanylpyridin-3-yl)acryloylamino]thiazole-5-carboxylic acid: m/z (ES+)=416.1 [M+H]+. Oxidation of this thioether, utilising an approach similar to that described in EXAMPLE 35, afforded 2-[3-cyclopentyl-2-(6-cyclopropanesulfonylpyridin-3-yl)acryloylamino]thiazole-5-carboxylic acid: m/z (ES+)=448.2 [M+H]+. This carboxylic acid (52 mg, 116 μmol) was condensed with MeNH2.HCl in the presence of NEt3, utilising the general procedure described in EXAMPLE 12, to give the title compound: RTA=3.29 min; m/z (ES+)=461.3 [M+H]+.

Sources & evidence

ORD record
ord-cf4ffac094f948b1b40a96ba07d152ae
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

Loading…