Water → Avanafil Impurity 37

HRID 2200867Notes

Reaction equation

HRID 2200867 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1.C1C=C(Cl)C=C(C(OO)=[O:31])C=1.O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]([S:16]([CH3:17])=[O:31])[N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 226655724-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid

Product 1

HCID 118157672Avanafil Impurity 37

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In DCM (20 mL) was dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio) pyrimidine-5-carboxylic acid (200 mg, 0.59 mmol). The solution was cooled in an ice bath and m-CPBA (101 mg, 0.59 mmol) was then added. The reaction was warmed to ambient temperature for 5 h. Then water was added and the reaction mixture was extracted with DCM. The organic phase was dried and concentrated to give a solid. The product was used in the subsequent procedure without further purification.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. extractionthe reaction mixture was extracted with DCM
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe product was used in the subsequent procedure without further purification

Sources & evidence

ORD record
ord-2456c0504bba476a9c958a00ca973a35
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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