Formaldehyde → HCID 54698207, compound

HRID 2214532Notes

Reaction equation

HRID 2214532 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[CH3:23][O:24][C:25](=[O:29])[CH2:26][CH2:27][NH2:28].[Cl:30][C:31]1[CH:32]=[C:33]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:34][N:35]([CH3:46])[C:36]([C:38]1[CH2:39]N(C)[C:41](=[O:44])[C:42]=1[OH:43])=[O:37]>>[CH3:23][O:24][C:25](=[O:29])[CH2:26][CH2:27][N:28]1[CH2:39][C:38]([C:36](=[O:37])[N:35]([CH2:34][C:33]2[CH:47]=[CH:48][C:49]([Cl:50])=[C:31]([Cl:30])[CH:32]=2)[CH3:46])=[C:42]([OH:43])[C:41]1=[O:44]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 192794Methyl beta-alanateHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 54698207HCID 54698207, compoundYield 17%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and β-alanine methyl ester 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 (34.3 mg, 17% yield). 1H NMR (300 MHz, CDCl3) δ: 7.41 (m, 2H), 7.09 (m, 1H), 4.59 (s, 2H), 4.27 (s, 2H), 3.77 (m, 2H), 3.67 (s, 3H), 3.03 (s, 3H), 2.69 (t, 2H, J=6.22). HRMS (M+H) calcd for C17H19N2Cl2O5: 401.0671. found: 401.0669.

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-7665fd228e584d7e9f3088ef44e4da8c
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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