1,1'-Carbonyldiimidazole → 2-(4-butyl-2-fluoroanilino)-3,4-difluoro-N-(2-hydroxyethoxy)benzamide

HRID 2181479Notes

Reaction equation

HRID 2181479 reaction equation
[CH2:1]([C:5]1[CH:22]=[CH:21][C:8]([NH:9][C:10]2[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)=[C:7]([F:23])[CH:6]=1)[CH2:2][CH2:3][CH3:4].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:36][O:37][CH2:38][CH2:39][OH:40]>>[CH2:1]([C:5]1[CH:22]=[CH:21][C:8]([NH:9][C:10]2[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:11]=2[C:12]([NH:36][O:37][CH2:38][CH2:39][OH:40])=[O:14])=[C:7]([F:23])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3014186Ethanol, 2-(aminooxy)-HCID 220256902-(4-Butyl-2-fluoroanilino)-3,4-difluorobenzoic acid

Product 1

HCID 101505162-(4-butyl-2-fluoroanilino)-3,4-difluoro-N-(2-hydroxyethoxy)benzamideYield 68%

Procedure

The title compound was prepared from reaction of 2-(4-butyl-2-fluoroanilino)-3,4-difluorobenzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E, then purified by flash column chromatography on silica (50% EtOAc/Hexane as eluant) to give 2-(4-butyl-2-fluoroanilino)-3,4-difluoro-N-(2-hydroxyethoxy)benzamide as a white solid (68%); m.p. (EtOAc/Hexane) 163-165° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.85 (br s, 1 H), 8.74 (br s, 1 H), 7.44-7.38 (m, 1 H), 7.14-7.06 (m, 1 H), 7.06-7.01 (m, 1 H), 6.88 (dd, J=8.3, 1.1 Hz, 1 H), 6.83 (ddd, J=8.4, 8.4, 4.2 Hz, 1 H), 4.73 (br s, 1 H), 3.87 (t, J=4.8 Hz, 2 H), 3.58 (t, J=4.8 Hz, 2 H), 2.52 (t, J=7.5 Hz, 2 H), 1.57-1.48 (m, 2 H), 1.29 (sextet, J=7.3 Hz, 2 H), 0.89 (t, J=7.3 Hz, 3 H). Anal. Calcd for C17H15F3N2O3: C, 59.7; H, 5.5; N, 7.3. Found C, 59.4; H, 5.4; N, 7.4.

Workup

  1. custompurified by flash column chromatography on silica (50% EtOAc/Hexane as eluant)

Sources & evidence

ORD record
ord-ee939e66eefa4f7a8592ff0913b1b0ab
Source dataset
uspto-grants-2005_05
Patent number
US06891066B2

Reaction notes

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