2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-methyl-n-(4-trifluoromethylbenzyl)-acetamide → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methyl-(4-trifluoromethyl-benzyl)-amide

HRID 2214714Notes

Reaction equation

HRID 2214714 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH3:22])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[O:9])[C:4](=[O:23])O1.[CH2:25]=O.[NH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CO>[CH3:22][N:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=1)[C:8]([C:7]1[CH2:25][N:27]([CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[C:4](=[O:23])[C:5]=1[OH:6])=[O:9]

Participants

4

Reactant 2

HCID 696554872-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-methyl-n-(4-trifluoromethylbenzyl)-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046174-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methyl-(4-trifluoromethyl-benzyl)-amideYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methyl-N-(4-trifluoromethyl-benzyl)-acetamide (0.36 g, 1.05 mmol) with the paraformaldehyde-N-(2-aminoethyl)morpholine adduct in methanol using a procedure similar to the one described in the preparation of compound 13 gave 0.16 g (35% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (CDCl3) δ (ppm); 2.46 (4H, m, 2×NCH2), 2.57 (2H, t, J=6.1 Hz, NCH2), 3.04 (3H, s, NCH3), 3.6 (6H, m, 2×OCH2 and NCH2), 4.25 (2H, s, NCH2), 4.72 (2H, s, NCH2), 7.41 (2H, d, J=8.0 Hz, aromatics), 7.62 (2H, d, J=8.0 Hz, aromatics). HRMS (FAB+) calculated for C20H25F3N3O4: [M+H]+: 428.179716. found: 428.179157.

Sources & evidence

ORD record
ord-a0b3a3d41d264302970023effa5dc9b0
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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