Formaldehyde → HCID 86760251, compound

HRID 2214528Notes

Reaction equation

HRID 2214528 reaction equation
CO[C:3](=[O:20])[C:4]([OH:19])=[CH:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)[CH3:8].C=O.[S:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1.CN.ClC1C=[C:33](C=CC=1Cl)[CH2:34][N:35](C)C(C1CN(C)C(=O)C=1O)=O>>[Cl:17][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[Cl:16])[CH2:9][N:7]([CH3:8])[C:6]([C:5]1[CH:34]([CH3:33])[N:35]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[C:3](=[O:20])[C:4]=1[OH:19])=[O:18]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 21947553HCID 21947553, compoundHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 86760251HCID 86760251, compoundYield 28%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and methylamine thiophene 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 (58.7 mg, 28% yield). 1H NMR (300 MHz, CDCl3) δ: 7.41 (d, 1H, J=8.05), 7.33 (d, 1H, J=1.83), 7.26 (m, 1H), 7.08 (dd, 1H, J=8.05, J=1.83), 6.97 (m, 2H), 4.85 (s, 2H), 4.57 (s, 2H), 4.11 (s, 2H), 3.00 (s, 3H). HRMS (M−H) calcd for C18H15SN2Cl2O3: 409.0180. found: 409.0190.

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-f65a16c3212a4b9994df1aaa00d8392e
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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