2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-[3-(4-fluorophenyl)-propyl]-N-methyl-acetamide → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid [3-(4-fluorophenyl)-propyl]-methyl-amide

HRID 2214723Notes

Reaction equation

HRID 2214723 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:11])=[O:9])[C:4](=[O:22])O1.[CH2:24]=O.[NH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CO>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][N:10]([CH3:11])[C:8]([C:7]2[CH2:24][N:26]([CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:4](=[O:22])[C:5]=2[OH:6])=[O:9])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 696561982-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-[3-(4-fluorophenyl)-propyl]-N-methyl-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046684-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid [3-(4-fluorophenyl)-propyl]-methyl-amideYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-[3-(4-fluorophenyl)-propyl]-N-methyl-acetamide (0.245 g, 0.76 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 0.103 g (33% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (CDCl3) δ (ppm); 1.92 (2H, m, CH2), 2.47 (4H, broad, 2×NCH2), 2.54 (2H, broad t, NCH2), 2.63 (2H, t, J=7.5 Hz, CH2), 3.04 (3H, s, NCH3), 3.42 (2H, broad t, NCH2), 3.58 (2H, broad, NCH2), 3.66 (4H, broad, 2×OCH2), 4.12 (2H, broad s, NCH2), 6.97 (2H, m, aromatics), 7.14 (2H, m, aromatics). HRMS (FAB+) calculated for C21H29FN3O4: [M+H]+: 406.214210. found: 406.214016.

Sources & evidence

ORD record
ord-c3cabb984a844410997656bba7fde9fc
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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