Formaldehyde → HCID 69656028, compound

HRID 2214531Notes

Reaction equation

HRID 2214531 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4](O)=[CH:5]C(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.Cl.NCCCC(O)=O.Cl[C:32]1[CH:33]=[C:34]([CH:48]=[CH:49][C:50]=1Cl)[CH2:35][N:36]([CH3:47])[C:37]([C:39]1[CH2:40][N:41]([CH3:46])[C:42](=[O:45])[C:43]=1[OH:44])=[O:38]>>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:46][N:41]1[CH2:40][C:39]([C:37](=[O:38])[N:36]([CH2:35][C:34]2[CH:48]=[CH:49][CH2:50][CH2:32][CH:33]=2)[CH3:47])=[C:43]([OH:44])[C:42]1=[O:45]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 210329gamma-Aminobutyric acid hydrochlorideHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 69656028HCID 69656028, compoundYield 9%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and 4-aminobutyrate hydrochloride 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 an amber oil (18.9 mg, 9% yield). 1H NMR (300 MHz, CDCl3) δ: 7.41 (m, 2H), 7.09 (m, 1H), 4.60 (s, 2H), 4.18 (s, 2H), 3.65 (s, 3H), 3.55 (t, 2H, J=7.32), 3.03 (s, 3H), 2.36 (t, 2H, J=7.32), 1.94 (t, 2H, J=6.95). HRMS (M+H) calcd for C18H21N2Cl2O53: 415.0827. found: 415.0831.

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-3e8a5f5d7a4644b9aeacefd1858a55ea
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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