HCID 12135109, compound → HCID 22025611, compound

HRID 2181466Notes

Reaction equation

HRID 2181466 reaction equation
[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][O:22][CH3:23])=[CH:15][C:14]=2[F:24])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6]>C(O)C.[Pd]>[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][C:14]=2[F:24])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 12135109HCID 12135109, compound

Product 1

HCID 22025611HCID 22025611, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of Example 25, Step B, 3,4-difluoro-2-[[2-fluoro-4-(3-methoxy-1-propynyl)phenyl]amino]benzoic acid, was hydrogenated in absolute ethanol in the presence of 5% Pd/C as above in Example 1, Step D. The resulting crude solid was purified by filtration through a plug of silica gel (50% EtOAc/hexanes as eluant) to give 3,4-difluoro-2-[[2-fluoro-4-(3-methoxypropyl)phenyl]amino]benzoic acid as a white solid (65%); m.p. (Et2O/hexanes) 125-127° C. 1H NMR [400 MHz, (CD3)2SO] δ 13.35 (br s, 1 H), 9.27 (br s, 1 H), 7.82 (ddd, J=8.3, 6.1, 1.9 Hz, 1 H), 7.08 (dd, J=12.4, 1.7 Hz, 1 H), 7.05-6.96 (m, 2 H), 6.93 (dd, J=8.2, 1.8 Hz, 1 H), 3.33 (t, J=6.4 Hz, 2 H), 3.23 (s, 3 H), 2.59 (t, J=7.7 Hz, 2 H), 1.83-1.73 (m, 2 H). Anal. Calcd for C17H16F3NO3: C, 60.2; H, 4.8; N, 4.1. Found: C, 60.2; H, 4.7; N, 4.1.

Workup

  1. filtrationThe resulting crude solid was purified by filtration through a plug of silica gel (50% EtOAc/hexanes as eluant)

Sources & evidence

ORD record
ord-7e9592735ec547ee8180d59050e37997
Source dataset
uspto-grants-2005_05
Patent number
US06891066B2

Reaction notes

Loading…