Formaldehyde → HCID 54698224, compound

HRID 2214596Notes

Reaction equation

HRID 2214596 reaction equation
CO[C:3](=[O:23])[C:4]([OH:22])=[CH:5][C:6](=[O:21])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[O:8][CH2:9][CH:10]([CH3:12])[CH3:11].C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:32][N:33](C)[C:34](C1CN(C)C(=O)C=1O)=O>>[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:7]([O:8][CH2:9][CH:10]([CH3:11])[CH3:12])[C:6]([C:5]2[CH2:32][N:33]([CH3:34])[C:3](=[O:23])[C:4]=2[OH:22])=[O:21])=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 72395064HCID 72395064, compound

Product 1

HCID 54698224HCID 54698224, compoundYield 40%

Procedure

3-[(4-Fluorobenzyl)-isobutoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 58-D) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (40% yield); mp 96–97° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 0.98 (6H, d, J=6.5 Hz, CH3), 1.96 (1H, m CH), 3.12 (3H, s, NCH3), 3.69 (2H, d, J=6.4 Hz, OCH2), 4.1 (2H, s, NCH2), 4.85 (2H, s, NCH2), 7.06 (2H, m, aromatics), 7.33 (2H, m, aromatics), 11.65 (1H, broad s, OH). HRMS (ES+) calculated for C17H22FN2O4, [M+H]+: 337.156361. found: 337.156153.

Sources & evidence

ORD record
ord-f7380be8005c4bb6ae00870da156fe19
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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