HCID 10193807, compound → HCID 10126260, compound

HRID 2181476Notes

Reaction equation

HRID 2181476 reaction equation
[CH2:1]([C:4]1[CH:25]=[CH:24][C:7]([NH:8][C:9]2[C:21]([F:22])=[C:20]([F:23])[CH:19]=[CH:18][C:10]=2[C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12])=[C:6]([F:26])[CH:5]=1)[CH:2]=[CH2:3]>CCO.[Pd]>[F:22][C:21]1[C:9]([NH:8][C:7]2[CH:24]=[CH:25][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][C:6]=2[F:26])=[C:10]([CH:18]=[CH:19][C:20]=1[F:23])[C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12]

Participants

4

Reactant 1

HCID 10193807HCID 10193807, compound

Product 1

HCID 10126260HCID 10126260, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

The product of Example 6, 2-(4-Allyl-2-fluoroanilino)-3,4-difluoro-N-(2-hydroxyethoxy)benzamide was dissolved in absolute EtOH and hydrogenated in the presence of 5% Pd/C by the procedure of Example 1, Step D. Purification of the resulting oil was carried out by filtration through a plug of silica gel (50% EtOAc/PE as eluant) to give 3,4-difluoro-2-(2-fluoro-4-propylanilino)-N-(2-hydroxyethoxy)benzamide as a white solid (77%); m.p. (EtOAc/hexane) 144-146° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.85 (br s, 1 H), 8.76 (br s, 1 H), 7.43-7.33 (m, 1 H), 7.14-7.06 (m, 1 H), 7.04 (dd, J=12.5, 1.5 Hz, 1 H), 6.88 (dd, J=8.3, 1.7 Hz, 1 H), 6.83 (ddd, J=8.6, 8.6, 4.2 Hz, 1 H), 4.70 (br s, 1 H), 3.86 (t, J=4.9 Hz, 2 H), 3.57 (t, J=4.9 Hz, 2 H), 2.49 (t, J=7.7 Hz, 2 H), 1.56 (sextet, J=7.4 Hz, 2 H), 0.87 (t, J=7.3 Hz, 3 H). Anal. calcd. for C18H19F3N2O3:C, 58.7; H, 5.2; N, 7.6. Found C, 58.8; H, 5.2; N, 7.7.

Workup

  1. customPurification of the resulting oil
  2. filtrationwas carried out by filtration through a plug of silica gel (50% EtOAc/PE as eluant)

Sources & evidence

ORD record
ord-198f995e41f243eab145541b114b9937
Source dataset
uspto-grants-2005_05
Patent number
US06891066B2

Reaction notes

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