Potassium Carbonate → HCID 86711637, compound

HRID 527369Notes

Reaction equation

HRID 527369 reaction equation
[CH:1]1([S:4]([C:8]2[CH:38]=[CH:37][C:11]([CH2:12][NH:13][C:14]([C:16]3[C:21](=[O:22])[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)=[C:19]([CH3:33])[N:18]([CH:34]([CH3:36])[CH3:35])[CH:17]=3)=[O:15])=[CH:10][CH:9]=2)=[N:5][C:6]#[N:7])[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:44].C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C>[CH:1]1([S:4]([C:8]2[CH:38]=[CH:37][C:11]([CH2:12][NH:13][C:14]([C:16]3[C:21](=[O:22])[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)=[C:19]([CH3:33])[N:18]([CH:34]([CH3:36])[CH3:35])[CH:17]=3)=[O:15])=[CH:10][CH:9]=2)(=[N:5][C:6]#[N:7])=[O:44])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 86711636HCID 86711636, compound

Product 1

HCID 86711637HCID 86711637, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-isopropyl-6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 4-(S-cyclopropyl-N-cyanosulfinimidoyl)-benzylamide (preparation 63d, 40 mg, 74 μmol), meta-chloroperoxybenzoic acid (77%, 25 mg, 0.11 mmol) and potassium carbonate (31 mg, 0.22 mmol) in ethanol is stirred at room temperature for 1 h. Another portion of meta-chloroperoxybenzoic acid (77%, 5 mg, ai 0.02 mmol) is added and stirring is continued for 1.5 h. Saturated aqueous sodium thiosulfate solution is added, and the mixture is extracted with dichloromethane. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% TFA). Yield: 13 mg (31% of theory); ESI mass spectrum: [M+H]+=557; r.t. HPLC: 0.65 min (X011_S03).

Workup

  1. stirringstirring
  2. waitis continued for 1.5 h
  3. extractionthe mixture is extracted with dichloromethane
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by preparative reversed phase HPLC (Xbridge, gradient of acetonitrile in water, 0.1% TFA)
  7. customr.t
  8. custom0.65 min (X011_S03)

Sources & evidence

ORD record
ord-45128f07fb234d979358bf89d322b178
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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