1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2-Methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid ethyl ester

HRID 1269552Notes

Reaction equation

HRID 1269552 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[CH:10]=[CH:9][C:8]=1[CH3:19])[CH3:2].CN(C)CCCN=C=NCC.[CH3:32][C:33]1[N:34]=[C:35]([C:41]2[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=2)[S:36][C:37]=1[C:38](O)=[O:39]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:38]([C:37]3[S:36][C:35]([C:41]4[CH:42]=[CH:43][C:44]([C:47]([F:50])([F:48])[F:49])=[CH:45][CH:46]=4)=[N:34][C:33]=3[CH3:32])=[O:39])[CH2:14]2)[CH:10]=[CH:9][C:8]=1[CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27756634-Methyl-2-(4-(trifluoromethyl)phenyl)-5-thiazolecarboxylic acidHCID 68883656(2-Methyl-5-piperidin-3-ylphenylamino)acetic acid ethyl ester

Product 1

HCID 68884771(2-Methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid ethyl esterYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Methyl-5-piperidin-3-yl-phenylamino)-acetic acid ethyl ester (Example 13-1; 63 mg, 0.23 mmol) was dissolved in 2 mL CH2Cl2 and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (87 mg, 0.46 mmol) and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acid (65 mg, 0.23 mmol) were added. The reaction was stirred at ambient temperature under nitrogen for 24 h. The reaction was flash chromatographed with 30% ethyl acetate/hexanes to yield 19 mg (15%) of the desired (2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid ethyl ester as a clear oil.

Workup

  1. customchromatographed with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a1e6da661d834d81a7307aaa66e115e4
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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