4-({[2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl]-methoxy-amino}-methyl)-n-methyl-benzamide → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methoxy-(4-methylcarbamoyl-benzyl)-amide

HRID 2214717Notes

Reaction equation

HRID 2214717 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([NH:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=[O:24])O1.[CH2:26]=O.[NH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>CO>[CH3:12][O:11][N:10]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:18](=[O:19])[NH:20][CH3:21])=[CH:22][CH:23]=1)[C:8]([C:7]1[CH2:26][N:28]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[C:4](=[O:24])[C:5]=1[OH:6])=[O:9]

Participants

4

Reactant 2

HCID 738555444-({[2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl]-methoxy-amino}-methyl)-n-methyl-benzamideHCID 86760256paraformaldehyde N-(2-aminoethyl)morpholine

Product 1

HCID 547046164-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid methoxy-(4-methylcarbamoyl-benzyl)-amideYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reaction 4-({[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl]-methoxy-amino}-methyl)-N-methyl-benzamide (0.053 g, 0.15 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 0.034 g (41% yield) of the title compound as a white solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (DMSO-d6) δ (ppm); (TFA salt) 2.77 (3H, d, J=4.65 Hz, NCH3), 3.1 (2H, broad m, NCH2), 3.4–3.8 (8H, broad m, 2×NCH2 and 2×OCH2), 3.75 (3H, s, OCH2), 3.98 (2H, broad, NCH2), 4.24 (2H, s, NCH2), 4.94 (2H, s, NCH2), 7.39 (2H, d, J=8.4 Hz, aromatics), 7.80 (2H, d, J=8.4 Hz, aromatic), 8.41 (1H, q, J=4.5 Hz, NH). HRMS (FAB+) calculated for C21H29N4O6: [M+H]+: 433.208710. found: 433.209419.

Sources & evidence

ORD record
ord-49c96b4c350a4b15908cf802ba5c658c
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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