m-Chloroperbenzoic acid → HCID 178518519, compound

HRID 624733Notes

Reaction equation

HRID 624733 reaction equation
[CH2:1]([S:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([CH:18]=[C:19]3[NH:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[C:13]2[N:12]=[C:11]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl>[CH2:1]([S:8]([C:9]1[N:14]2[N:15]=[CH:16][C:17]([CH:18]=[C:19]3[NH:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[C:13]2[N:12]=[C:11]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[CH:10]=1)=[O:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178518518HCID 178518518, compound

Product 1

HCID 178518519HCID 178518519, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the reaction flask, 5-((7-(benzylthio)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (4.1 g, 8.6 mmol) was added to dichloromethane (86 mL) along with m-chloroperbenzoic acid (5.9 g, 34.4 mmol). The mixture was allowed to stir at room temperature for 12 hours. The solid was collected by filtration, washed with dichloromethane then dried under vacuum overnight. The product, 5-((7-(benzylsulfinyl)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was recovered as a bright yellow solid in quantitative yield. LCMS (M+1=493)

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with dichloromethane
  3. customthen dried under vacuum overnight
  4. customThe product, 5-((7-(benzylsulfinyl)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was recovered as a bright yellow solid in quantitative yield

Sources & evidence

ORD record
ord-0ce42957443c4be1830b02daccd3e099
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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