Formaldehyde → N-[(4-acetamidophenyl)methyl]-4-hydroxy-N-methoxy-1-methyl-5-oxo-2H-pyrrole-3-carboxamide

HRID 2214617Notes

Reaction equation

CO[C:3](=[O:23])[C:4]([OH:22])=[CH:5][C:6](=[O:21])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[CH:13][CH:12]=1)[O:8][CH3:9].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:32][N:33](C)[C:34](C1CN(C)C(=O)C=1O)=O>>[C:18]([NH:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]2[CH2:32][N:33]([CH3:34])[C:3](=[O:23])[C:4]=2[OH:22])=[O:21])=[CH:16][CH:15]=1)(=[O:20])[CH3:19]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 6329Methylamine

HCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide

HCID 72395079HCID 72395079, compound

Product 1

HCID 54698229N-[(4-acetamidophenyl)methyl]-4-hydroxy-N-methoxy-1-methyl-5-oxo-2H-pyrrole-3-carboxamideYield 43%

Procedure

3-[(4-Acetylaminobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 63-D) was treated with paraformaldehyde and methylamine as described in the preparation Compound 12 to give the title compound as a white solid (43% yield); mp 110° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.18 (3H, s, COCH3), 3.1 (3H, s, NCH3), 3.71 (3H, s, OCH3), 4.15 (2H, s, NCH2), 4.83 (2H, s, NCH2), 7.29 (2H, d, J=8.6 Hz, aromatics), 7.34 (1H, broad s, NH), 7.50 (2H, d, J=8.6 Hz, aromatics). HRMS (ES+) calculated for C16H20N3O5: [M+H]+: 334.140296. found: 334.139137.

Sources & evidence

ORD record: ord-e40b576ee4794c309bab083748f57289
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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