m-Chloroperbenzoic acid → HCID 90310972, compound

HRID 927230Notes

Reaction equation

HRID 927230 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[O:12]=[C:13]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[C:17]2[CH2:29][CH2:30][C:31](=[O:32])[C:16]=2[CH:15]([C:33]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][C:34]=2[S:41][CH3:42])[NH:14]1.C([O-])(O)=O.[Na+]>ClCCl>[O:12]=[C:13]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[C:17]2[CH2:29][CH2:30][C:31](=[O:32])[C:16]=2[CH:15]([C:33]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][C:34]=2[S:41]([CH3:42])=[O:6])[NH:14]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 90310807HCID 90310807, compound

Product 1

HCID 90310972HCID 90310972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

meta-Chloroperoxybenzoic acid (77%, 390 mg, 1.74 mmol) is added at room temperature to a solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)-3-(methylthio)benzonitrile (example 16, 776 mg, 1.75 mmol) in dichloromethane, and the mixture is stirred for 30 min Saturated aqueous NaHCO3 solution is added, and the mixture is extracted with dichloromethane. The combined organic layers are concentrated under reduced pressure, and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate. Yield: 527 mg; ESI mass spectrum [M+H]+=460; Retention time HPLC: 0.48 min (early eluting diastereomer), 0.49 (late eluting diastereomer) (X012_S01).

Workup

  1. additionis added
  2. extractionthe mixture is extracted with dichloromethane
  3. concentrationThe combined organic layers are concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate
  5. washRetention time HPLC: 0.48 min (early eluting diastereomer), 0.49 (late eluting diastereomer) (X012_S01)

Sources & evidence

ORD record
ord-e824f5479eb545319f6a5fd44966f149
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

Loading…