Formaldehyde → HCID 54698227, compound

HRID 2214607Notes

Reaction equation

HRID 2214607 reaction equation
CO[C:3](=[O:22])[C:4]([OH:21])=[CH:5][C:6](=[O:20])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]#[N:19])[CH:12]=1)[O:8][CH3:9].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:31][N:32](C)[C:33](C1CN(C)C(=O)C=1O)=O>>[C:18]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[F:17])[CH2:10][N:7]([O:8][CH3:9])[C:6]([C:5]1[CH2:31][N:32]([CH3:33])[C:3](=[O:22])[C:4]=1[OH:21])=[O:20])#[N:19]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 86760252HCID 86760252, compound

Product 1

HCID 54698227HCID 54698227, compoundYield 69%

Procedure

3-[(3-Cyano-4-fluorobenzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 61-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (69% yield); mp 175° C. dec. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.11 (3H, s, NCH3), 3.78 (3H, s, OCH3), 4.16 (2H, s, NCH2), 4.85 (2H, s, NCH2), 7.19–7.24 (1H, m, aromatic), 7.59–7.62 (2H, m, aromatics).

Sources & evidence

ORD record
ord-d004cf4754cc4aeb8fb113397043755e
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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