Formaldehyde → N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-1-[2-(4-sulfamoylphenyl)ethyl]-2H-pyrrole-3-carboxamide

HRID 2214516Notes

Reaction equation

HRID 2214516 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[NH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1.[Cl:36][C:37]1[CH:38]=[C:39]([CH:53]=[CH:54][C:55]=1[Cl:56])[CH2:40][N:41]([CH3:52])[C:42]([C:44]1[CH2:45]N(C)[C:47](=[O:50])[C:48]=1[OH:49])=[O:43]>>[Cl:36][C:37]1[CH:38]=[C:39]([CH:53]=[CH:54][C:55]=1[Cl:56])[CH2:40][N:41]([CH3:52])[C:42]([C:44]1[CH2:45][N:23]([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([S:32](=[O:33])(=[O:34])[NH2:35])=[CH:30][CH:31]=2)[C:47](=[O:50])[C:48]=1[OH:49])=[O:43]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 54698196N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-1-[2-(4-sulfamoylphenyl)ethyl]-2H-pyrrole-3-carboxamideYield 19%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and 4-(2-amino-ethyl)benzenesulfonamide as described in the preparation of Compound 12. The resulting residue 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 (47.9 mg, 19% yield). Decomposition point=110–113° C. 1H NMR (500 MHz, DMSO) δ: 10.97 (s, 1H), 7.72, (m, 2H), 7.61 (d, 1H, J=8.54), 7.51 (s, 1H), 7.42 (m, 2H), 7.29 (m, 2H), 7.25, (m, 1H), 4.56, (s, 2H), 4.04, (s, 2H), 3.67 (m, 2H), 3.34 (m, 2H), 2.95 (d, 3H, J=6.41). HRMS (M−H) calcd for C21H20SN3Cl2O5: 496.0500. found: 496.0503.

Workup

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

Sources & evidence

ORD record
ord-497a2b2d27ea457bb14f92401d652ee5
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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