Water → Avanafil Impurity 37

HRID 2200883Notes

Reaction equation

HRID 2200883 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 6344DichloromethaneSolvent2×

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 added. The reaction was conducted at ambient temperature for 5 h, followed by addition of water and extraction with DCM. The organic phase was dried and concentrated to give a solid which was used in the subsequent procedure without further purification.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customto give a solid which
  5. customwas used in the subsequent procedure without further purification

Sources & evidence

ORD record
ord-9eb39b1c2ac1451d96871882c515cd6f
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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