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

HRID 2214730Notes

Reaction equation

HRID 2214730 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:9])[C:4](=[O:29])O1.[CH2:31]=O.[NH2:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CO>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:10]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[C:8]([C:7]2[CH2:31][N:33]([CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[C:4](=[O:29])[C:5]=2[OH:6])=[O:9])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 738555492-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluorobenzyl)-n-(3-morpholin-4-yl-propoxy)-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046934-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid (4-fluoro-benzyl)-(3-morpholin-4-yl-propoxy)-amideYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-(3-morpholin-4-yl-propoxy)-acetamide (0.080 g, 0.19 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 0.019 g (20% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (CDCl3) δ (ppm); 1.65 (2H, m, CH2), 2.25 (2H, t, J=7.3 Hz, NCH2), 2.29 (4H, broad, 2×NCH2), 2.39 (4H, broad, 2×NCH2), 2.46 (2H, t, J=6.6 Hz, CH2), 3.50 (2H, t, J=6.6 Hz, NCH2), 3.68 (8H, broad, 4×OCH2), 3.84 (2H, t, J=7.0 Hz, OCH2), 4.11 (2H, s, NCH2), 4.87 (2H, s, NCH2), 7.16 (2H, m, aromatics), 7.40 (2H, m, aromatics). HRMS (MAB N2) calculated for C25H35FN4O6: [M]+: 506.254064; found: 506.254892.

Sources & evidence

ORD record
ord-f8b730ca20374961bea8a8bddb831409
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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