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

HRID 2214545Notes

Reaction equation

HRID 2214545 reaction equation
CO[C:3](=[O:20])[C:4]([OH:19])=[CH:5][C:6](=[O:18])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[O:8][CH3:9].C=O.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.Cl[C:33]1C=C(C=CC=1Cl)CN(C)C(C1CN(CCN2CCOCC2)C(=O)C=1O)=O>>[F:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]2[CH2:33][N:23]([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:3](=[O:20])[C:4]=2[OH:19])=[O:18])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 8795AminoethylpiperazineHCID 54691036N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-1-(2-morpholinoethyl)-5-oxo-2H-pyrrole-3-carboxamideHCID 723950773-[(4-Fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester

Product 1

HCID 54698214N-[(4-fluorophenyl)methyl]-4-hydroxy-N-methoxy-5-oxo-1-(2-piperazin-1-ylethyl)-2H-pyrrole-3-carboxamideYield 4.3%

Procedure

3-[(4-Fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 44-D) was treated with paraformaldehyde and N-(2-aminoethyl)piperazine as described in the preparation of Compound 13. The mixture was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as a white powder (0.0110 g, 4.3% yield). 1H NMR (500 MHz, CDCl3) δ: 2.55 (t, J=6.2 Hz, 2H), 2.71 (s, 4H), 2.98 (s, 4H), 3.47 (t, J=5.5 Hz, 2H), 3.57 (s, 3H), 4.03 (s, 2H), 4.68 (s, 2H), 6.87 (s, 2H), 7.17 (m, 2H), 9.72 (bs, 1H), 11.45 (bs, 1H). HRMS (M+H) calcd for C19H25FN4O4: 391.17816. found: 391.1786.

Workup

  1. customThe mixture was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-e49df2eed54849029e77ad021a786a1e
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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