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

HRID 2214712Notes

Reaction equation

HRID 2214712 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([O:19][CH3:20])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[O:9])[C:4](=[O:21])O1.[CH2:23]=O.[NH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CO>[CH3:20][O:19][N:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[C:8]([C:7]1[CH2:23][N:25]([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:4](=[O:21])[C:5]=1[OH:6])=[O:9]

Participants

4

Reactant 2

HCID 738555682-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-methoxy-n-(4-methylbenzyl)-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046134-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methoxy-(4-methylbenzyl)-amideYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-N-(4-methylbenzyl)-acetamide (0.30 g, 0.98 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 0.17 g (45% yield) of the title compound as a solid. 1HNMR 400 MHz (CDCl3) δ (ppm); 2.35 (3H, s, CH3), 2.47 (4H, m, 2×NCH2), 2.56 (2H, t, J=6.2 Hz, NCH2), 3.62 (2H, t, J=6.2 Hz, NCH2), 3.66 (4H, m, 2×OCH2), 3.71 (3H, s, OCH3), 4.27 (2H, s, NCH2), 4.85 (2H, s, NCH2), 7.14–7.24 (4H, m, aromatics). HRMS (FAB+) calculated for C20H28N3O5: [M+H]+: 390.202896. found: 390.203567.

Sources & evidence

ORD record
ord-6e442f315f31498fb42f2e56777a7b39
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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