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

HRID 2214727Notes

Reaction equation

HRID 2214727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]([O:24][CH3:25])[C:13](=[O:23])[CH:14]=[C:15]2[C:19](=[O:20])OC(C)(C)[O:16]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:26]=O.[NH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]([O:24][CH3:25])[C:13]([C:14]2[CH2:26][N:28]([CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:19](=[O:20])[C:15]=2[OH:16])=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 73855586n-[3-(3,4-Dichloro-phenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-n-methoxy-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046244-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(3,4-dichlorophenyl)-propyl]-methoxy-amideYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of N-[3-(3,4-dichlorophenyl)-propyl]-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-acetamide (0.378 g, 0.97 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 0.196 g (42% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (CDCl3) δ (ppm); 1.98 (2H, m, CH2), 2.49 (4H, broad, 2×NCH2), 2.58 (2H, t, J=6.2 Hz, CH2), 2.63 (2H, t, J=7.5 Hz, CH2), 3.63 (2H, t, J=6.2 Hz, NCH2), 3.68 (4H, broad, 2×OCH2), 3.71 (3H, s, OCH3), 3.74 (2H, t, J=7.0 Hz, NCH2), 4.23 (2H, s, NCH2), 7.02 (1H, dd, J=2.0 Hz and J=8.2 Hz, aromatic), 7.28 (1H, d, J=2.0 Hz, aromatic), 7.34 (1H, d, J=8.2 Hz, aromatic). HRMS (FAB+) calculated for C21H28Cl2N3O5: [M+H]+: 472.140602. found: 472.138651.

Sources & evidence

ORD record
ord-d635eb78e3514112bbf9533548997041
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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