Methanol → 4-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid (4-fluoro-benzyl)-(3-morpholin-4-yl-propoxy)-amide

HRID 2214729Notes

Reaction equation

HRID 2214729 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.C=O.[CH3:33][NH2:34].[CH3:35]O>>[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[CH2:33][N:34]([CH3:35])[C:4](=[O:29])[C:5]=2[OH:6])=[O:9])=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 22018472Paraformaldehyde methylamineHCID 738555492-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluorobenzyl)-n-(3-morpholin-4-yl-propoxy)-acetamide

Product 1

HCID 547046944-Hydroxy-1-methyl-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid (4-fluoro-benzyl)-(3-morpholin-4-yl-propoxy)-amideYield 35%

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, 0.18 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 0.027 g (35% yield) of the title compound as a white solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (DMSO-d6) δ (ppm); 1.61 (2H, m, CH2), 2.23 (2H, t, J=7.0 Hz, NCH2), 2.28 (4H, broad, 2×NCH2), 2.93 (3H, s, NCH3), 3.54 (4H, broad, 2×OCH2), 3.76 (2H, broad t, OCH2), 3.97 (2H, s, NCH2), 4.88 (2H, s, NCH2), 7.13 (2H, m, aromatics), 7.40 (2H, m, aromatics). HRMS (MAB N2) calculated for C20H26FN3O5: [M]+: 407.185650. found: 407.184331.

Sources & evidence

ORD record
ord-afaad65632264df59471dd3c3801df30
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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