Dimethyl Sulfoxide → HCID 57756272, compound

HRID 593949Notes

Reaction equation

HRID 593949 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.CS(C)=[O:25].OO.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH2:20])=[O:25])[CH:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen Peroxide2×HCID 11430Potassium Carbonate2×HCID 66732025HCID 66732025, compound

Product 1

HCID 57756272HCID 57756272, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to the reference: Katritzky, A. R.; Pilarski, B.; Urogdi, L. Synthesis 1989, 949. As described, a solution of 4-(2-(4-aminophenoxy)pyridin-3-yl)picolinonitrile (764 mg, 2.65 mmol) in DMSO (0.883 mL, 2.65 mmol) was cooled to 0° C. 2.7 mL of 30% Hydrogen peroxide in water was added followed by potassium carbonate (37 mg, 0.27 mmol). The solution became a thick, milky white suspension. The mixture was warmed to rt. After 10 min, 1 mL of H2O2 and 20 mg of K2CO3 were added. After 20 min, LC-MS showed that the reaction was completed. The white solid was filtered off and washed with water. The product was dried under vacuum, to afford 4-(2-(4-aminophenoxy)pyridin-3-yl)picolinamide. MS m/z=307 [M+1]+. Calcd for C17H14N4O2: 306.11.

Workup

  1. customThe title compound was prepared
  2. customSynthesis 1989, 949
  3. waitAfter 20 min
  4. filtrationThe white solid was filtered off
  5. washwashed with water
  6. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-49291d0175544ec0a2e256ef5e2b6a53
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

Loading…