Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(4-fluorophenyl)-propyl]-methyl-amide

HRID 2214722Notes

Reaction equation

HRID 2214722 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.C=O.[CH3:26][NH2:27].[CH3:28]O>>[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[CH2:26][N:27]([CH3:28])[C:4](=[O:22])[C:5]=2[OH:6])=[O:9])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 22018472Paraformaldehyde methylamineHCID 696561982-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-[3-(4-fluorophenyl)-propyl]-N-methyl-acetamide

Product 1

HCID 547046664-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid [3-(4-fluorophenyl)-propyl]-methyl-amideYield 56%

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-[3-(4-fluorophenyl)-propyl]-N-methyl-acetamide (0.20 g, 0.62 mmol) with the paraformaldehyde-methylamine adduct in methanol using a procedure similar to the one described in the preparation of compound 44 (method 44B) gave 0.11 g (56% yield) of the title compound as white crystals; mp 129° C. (dec) (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm); 1.91 (2H, m, CH2), 2.63 (2H, t, J=7.6 Hz, CH2), 3.04 (3H, s, NCH3), 3.05 (3H, s, NCH3), 3.40 (2H, broad t, J=7.5 Hz, NCH2), 3.90 (2H, broad s, NCH2), 6.99 (2H, m, aromatics), 7.14 (2H, m, aromatics). Anal. Calcd for C16H19FN2O3: C, 62.73; H, 6.25; N, 9.14. Found: C, 62.75; H, 6.23; N, 9.11.

Sources & evidence

ORD record
ord-fe0c9e34a66540ef81a3249a49593643
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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