Dimethyl Sulfoxide → HCID 57756272, compound

HRID 2361040Notes

Reaction equation

HRID 2361040 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-7834cdd3e0394007a0100e5e4090c83d
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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