Formaldehyde → HCID 86760250, compound

HRID 2214520Notes

Reaction equation

HRID 2214520 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.NCC1C=CN=CC=1.ClC1C=[C:34](C=CC=1Cl)[CH2:35][N:36](C)[C:37]([C:39]1[CH2:40][N:41](C)[C:42](=O)[C:43]=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:35]([CH3:34])[N:36]([C:37]2[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=2)[C:3](=[O:20])[C:4]=1[OH:19])=[O:18]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 773174-PyridinemethanamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 86760250HCID 86760250, compoundYield 5%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and 4-(amino-methyl)pyridine 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 sticky orange solid (10.5 mg, 5% yield). 1H NMR (300 MHz, DMSO) δ: 8.75 (d, 2H, J=6.22), 7.63–7.52 (m, 4H), 7.25 (d, 2H, J=7.31), 4.80 (s, 2H), 4.59 (s, 2H), 4.1 (s, 2H), 2.99 (bs, 3H). HRMS (M−H) calcd for C19H16N3Cl2O3: 404.0568. found: 404.0554.

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-8bc13b6bbbd9411d9c7cf5917ec2b101
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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