Formaldehyde → HCID 54698237, compound

HRID 2214636Notes

Reaction equation

CO[C:3](=[O:25])[C:4]([OH:24])=[CH:5][C:6](=[O:23])[N:7]([O:16][CH2:17][C:18](=[O:22])[N:19]([CH3:21])[CH3:20])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:34][N:35](C)[C:36](C1CN(C)C(=O)C=1O)=O>>[CH3:21][N:19]([CH3:20])[C:18]([CH2:17][O:16][N:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=1)[C:6]([C:5]1[CH2:34][N:35]([CH3:36])[C:3](=[O:25])[C:4]=1[OH:24])=[O:23])=[O:22]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 6329Methylamine

HCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide

HCID 72395073HCID 72395073, compound2×

Product 1

HCID 54698237HCID 54698237, compoundYield 25%

Procedure

3-[Dimethylcarbamoylmethoxy-(4-fluorobenzyl)-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 72-B) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (25% yield); mp 147–149° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.79 (3H, s, NCH3), 2.96 (3H, s, NCH3), 3.11 (3H, s, NCH3), 4.25 (2H, s, CH2), 4.51 (2H, s, CH2), 4.96 (2H, s, CH2), 7.06 (2H, m, aromatics), 7.38 (2H, m, aromatics), 11.54 (1H, broad s, OH). HRMS (ES+) calculated for C17H21FN3O5, [M+H]+: 366.146524. found: 366.146176.

Sources & evidence

ORD record: ord-a227e9fcf5a74bbd9923af740b702c88
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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