Dimethyl Sulfoxide → HCID 44820353, compound

HRID 2273990Notes

Reaction equation

HRID 2273990 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][CH3:11])=[O:9])[CH:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:34])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>>[CH3:11][NH:10][C:8](=[O:9])[C:4]1[CH:3]=[C:2]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:34])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:17][CH:18]=2)[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 58533480HCID 58533480, compound

Product 1

HCID 44820353HCID 44820353, compound

Procedure

4-Chloro-N-methylpicolinamide (70 mg, 410 μmol), N-(4-hydroxyphenyl)-2-(phenylamino)benzamide (150 mg, 492 μmol), cesium carbonate (267 mg, 821 μmol), and DMSO (410 μl 410 μmol) were added into a screw-capped test tube. The tube was sealed and placed in a preheated oil bath at 130° C. After 16 h, LC-MS showed mainly desired product. Water was added, and a gray solid precipitated out of the solution. The solid was filtered off and rinsed with water. The product was purified by reverse phase preparative HPLC. Fractions containing the product were combined, neutralized with sat NaHCO3 (aq), washed with brine, dried over MgSO4, and concentrated in vacuo. The product, N-methyl-4-(4-(2-(phenylamino)benzamido)phenoxy)picolinamide was collected as a black solid. MS Calcd for C26H22N4O3: [M]+=438. Found: [M+H]+=439.

Workup

  1. customThe tube was sealed
  2. customplaced in a preheated oil bath at 130° C

Sources & evidence

ORD record
ord-98813ed74f99412ba69993ca937b5f3c
Source dataset
uspto-grants-2015_09
Patent number
US09126935B2

Reaction notes

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