1,1'-Carbonyldiimidazole → HCID 10216123, compound

HRID 1793038Notes

Reaction equation

HRID 1793038 reaction equation
[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.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:37][O:38][CH2:39][CH2:40][OH:41]>>[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]([NH:37][O:38][CH2:39][CH2:40][OH:41])=[O:7]

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3014186Ethanol, 2-(aminooxy)-HCID 22025611HCID 22025611, compound

Product 1

HCID 10216123HCID 10216123, compoundYield 69%

Procedure

The title compound was prepared from reaction of the product of Example 25, Step C, 3,4-difluoro-2-[[2-fluoro-4-(3-methoxypropyl)phenyl]amino]benzoic acid with CDI and 2-(aminooxy)ethanol, by the general procedure of Example 1, Step E, then purified by flash column chromatography on silica gel (50% EtOAc/hexanes) to give 3,4-difluoro-2-[[2-fluoro-4-(3-methoxypropyl)phenyl]-amino]-N-(2-hydroxyethoxy)benzamide as a cream solid (69%); m.p. (Et2O/hexanes) 136–137° C. 1H NMR [400 MHz, (CD3)2SO] δ 11.85 (br s, 1 H), 8.77 (br s, 1 H), 7.43–7.36 (m, 1 H), 7.15–7.00 (m, 2 H), 6.95–6.77 (m, 2 H), 4.71 (br s, 1 H), 3.85 (t, J=4.8, 2 H), 3.56 (t, J=4.8, 2 H), 3.33 (t, J=6.4 Hz, 2 H), 3.23 (s, 3 H), 2.56 (t, J=7.7 Hz, 2 H), 1.80–1.71 (m, 2 H).

Workup

  1. custompurified by flash column chromatography on silica gel (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-21ffa39c779d46b29f1fddda419cf3ee
Source dataset
uspto-grants-2006_07
Patent number
US07078438B2

Reaction notes

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