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

HRID 2214716Notes

Reaction equation

HRID 2214716 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([O:22][CH3:23])[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:24])O1.[CH2:26]=O.[NH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CO>[CH3:23][O: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[CH2:26][N:28]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[C:4](=[O:24])[C:5]=1[OH:6])=[O:9]

Participants

4

Reactant 2

HCID 738555482-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-methoxy-n-(4-trifluoromethylbenzyl)-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046124-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methoxy-(4-trifluoromethyl-benzyl)-amideYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-N-(4-trifluoromethyl-benzyl)-acetamide (0.41 g, 1.13 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 0.38 g (75% yield) of the title compound as crystals after chromatography on reversed phase silica gel; mp 119° C. (dec) (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 2.48 (4H, m, 2×NCH2), 2.58 (2H, t, J=6.3 Hz, NCH2), 3.64 (2H, t, J=6.3 Hz, NCH2), 3.67 (4H, m, 2×OCH2), 3.75 (3H, s, OCH3), 4.31 (2H, s, NCH2), 4.94 (2H, s, NCH2), 7.47 (2H, d, J=8.1 Hz, aromatics), 7.63 (2H, d, J=8.1 Hz, aromatics). Anal. Calcd for C20H24F3N3O5: C, 54.17; H, 5.46; N, 9.48. Found: C, 54.12; H, 5.57; N, 9.52.

Sources & evidence

ORD record
ord-cc4f2a8d3ddc4f6da1e0b86f6dc15270
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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