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

HRID 2214720Notes

Reaction equation

HRID 2214720 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]([F:24])([F:23])[F:22])[O:11][CH3:12])=[O:9])[C:4](=[O:25])O1.[CH2:27]=O.[NH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>CO>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]([O:11][CH3:12])[C:8]([C:7]2[CH2:27][N:29]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:4](=[O:25])[C:5]=2[OH:6])=[O:9])=[C:15]([C:21]([F:22])([F:23])[F:24])[CH:16]=1

Participants

4

Reactant 2

HCID 738555752-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluoro-2-trifluoromethyl-benzyl)-n-methoxy-acetamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046894-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid (4-fluoro-2-trifluoromethyl-benzyl)-methoxy-amideYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-(4-fluoro-2-trifluoromethyl-benzyl)-N-methoxy-acetamide (0.21 g, 0.55 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 0.13 g (50% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (CDCl3) δ (ppm); 2.51 (4H, m, 2×NCH2), 2.60 (2H, t, J=6.1 Hz, NCH2), 3.65 (6H, m, 2×OCH2 and NCH2), 3.71 (3H, s, OCH3), 4.32 (2H, s, NCH2), 5.09 (2H, s, NCH2), 7.23–7.27 (2H, m, aromatics), 7.39–7.48 (2H, m, aromatics). MS (ESI+) calculated for C20H24F4N3O5: [M+H]+: 462. found: 462.

Sources & evidence

ORD record
ord-dea3778358ce4fb59cdb5600b2357146
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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