1,1'-Carbonyldiimidazole → 3,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide

HRID 1793045Notes

Reaction equation

HRID 1793045 reaction equation
[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([S:19][CH2:20][CH3:21])=[CH:15][C:14]=2[F:22])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:35][O:36][CH2:37][CH2:38][OH:39]>>[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([S:19][CH2:20][CH3:21])=[CH:15][C:14]=2[F:22])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH:35][O:36][CH2:37][CH2:38][OH:39])=[O:7]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3014186Ethanol, 2-(aminooxy)-HCID 220256913,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]benzoic acid

Product 1

HCID 101940633,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamideYield 65%

Procedure

The title compound was prepared from reaction of the product of Example 27, Step B, 3,4-difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]benzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E. Then, after workup, the crude solid triturated with Et2O and washed with pentane to afford 3,4-difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide as a white solid (65%); m.p. (Et2O) 129–132° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.80 (br s, 1 H), 8.77 (br s, 1 H), 7.41 (ddd, J=9.0, 5.8, 2.1 Hz, 1 H), 7.23 (dd, J=11.8, 2.1 Hz, 1 H), 7.15 (ddd, J=9.9, 8.9, 7.2 Hz, 1 H), 7.04 (ddd, J=8.5, 2.1, 0.9 Hz, 1 H), 6.85 (ddd, J=9.9, 8.5, 4.2 Hz, 1 H), 4.72 (br s, 1 H), 3.85 (t, J=4.9 Hz, 2 H), 3.57 (t, J=4.9 Hz, 1 H), 2.92 (q, J=7.3 Hz, 2 H), 1.20 (t, J=7.3 Hz, 3 H). Anal. Calcd for C17H17F3N2O3S: C, 52.8; H, 4.4; N, 7.3. Found: C, 53.0; H, 4.7; N, 7.2.

Workup

  1. customThen, after workup, the crude solid triturated with Et2O
  2. washwashed with pentane

Sources & evidence

ORD record
ord-cafa73904e494338b7ca5974bfa59ba8
Source dataset
uspto-grants-2006_07
Patent number
US07078438B2

Reaction notes

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