Formaldehyde → HCID 54698200, compound

HRID 2214521Notes

Reaction equation

HRID 2214521 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[CH2:23]([O:25][P:26]([CH2:31][CH2:32][NH2:33])(=[O:30])[O:27][CH2:28][CH3:29])[CH3:24].[Cl:34][C:35]1[CH:36]=[C:37]([CH:51]=[CH:52][C:53]=1[Cl:54])[CH2:38][N:39]([CH3:50])[C:40]([C:42]1[CH2:43]N(C)[C:45](=[O:48])[C:46]=1[OH:47])=[O:41]>C(Cl)Cl.CCCCCC>[CH2:28]([O:27][P:26]([CH2:31][CH2:32][N:33]1[CH2:43][C:42]([C:40](=[O:41])[N:39]([CH2:38][C:37]2[CH:51]=[CH:52][C:53]([Cl:54])=[C:35]([Cl:34])[CH:36]=2)[CH3:50])=[C:46]([OH:47])[C:45]1=[O:48])(=[O:30])[O:25][CH2:23][CH3:24])[CH3:29]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 2733596Diethyl (2-aminoethyl)phosphonateHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 54698200HCID 54698200, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and (2-aminoethyl)phosphonic acid diethylester as described in the preparation of Compound 12. Trituration with CH2Cl2/hexane gave the title compound (106 mg, 44% yield). 1H NMR (300 MHz, CDCl3) δ: 7.41 (d, 1H, J=8.05), 7.35 (s, 1H), 7.10 (dd, 1H, J=8.05, J=1.47), 4.60 (s, 2H), 4.25 (s, 2H), 4.11 (m, 4H), 3.77 (m, 2H), 3.02 (s, 3H), 2.17 (m, 2H), 1.31 (t, 6H, J=7.32). HRMS (M−H) calcd for C19H24PN2Cl2O6: 477.0749. found: 477.0749.

Sources & evidence

ORD record
ord-11145abb8bb74e3690e995f53765e360
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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