Dimethyl Sulfoxide → 6-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-pyridin-3-ol

HRID 533925

Reaction equation

HRID 533925 reaction equation
CS(C)=O.[OH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=O)=[N:10][CH:11]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.O[NH:28][C:29](=[NH:33])[CH:30]([CH3:32])[CH3:31]>CC(=O)OCC>[CH:30]([C:29]1[N:33]=[C:12]([C:9]2[N:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)[O:14][N:28]=1)([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 682631,1'-CarbonyldiimidazoleHCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 178449908HCID 178449908, compound

Product 1

HCID 1363773006-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-pyridin-3-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To DMSO (25 mL) was added 5-hydroxy-pyridine-2-carboxylic acid (1.0 g) and CDI (1.3 g). After 15 minutes N-hydroxy-isobutyramidine (820 mg) was added. After 1 hour the mixture was heated to 90° C. for 1 hour. After the mixture reached room temperature, it was diluted with EA and washed three times with HCl (0.1 M). The organic phase was dried (Na2SO4) and concentrated to provide the title compound. MS ESI+: m/z=206 [M+H]+.

Workup

  1. customreached room temperature
  2. washwashed three times with HCl (0.1 M)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-989f920584734f61b7577085f4131722
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Linked notes

Loading…