Acetic Acid → HCID 89816264, compound

HRID 1500190Notes

Reaction equation

HRID 1500190 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[CH:19]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[CH2:18][CH2:17]4)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(=[O:34])C>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:30])([F:31])[F:29])[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[CH:19]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[CH2:18][CH2:17]4)[C:10]2=[O:34])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89815765HCID 89815765, compound

Product 1

HCID 89816264HCID 89816264, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 235.7 mg N-{5-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2,3-dihydro-1H-inden-1-yl}propanamide (0.5 mmol) in 20 ml toluene was added 1304 mg manganese(IV)dioxide (15.0 mmol) and stirred at 20° C. for 12 h. After standing for about 2 d at room temperature 100 μl acetic acid were added and the mixture stirred for 15.5 h. The reaction mixture was filtered through celite-silica gel. The crude product (198 mg) was subjected to silica gel column chromatography yielding 20 mg of compound (I-A-2) and 67 mg pure N-{5-[3-(3,5-dichlorophenyl)-2-oxo-3-(trifluoromethyl)pyrrolidin-1-yl]-2,3-dihydro-1H-inden-1-yl}propanamide (I-B-2).

Workup

  1. waitAfter standing for about 2 d at room temperature
  2. stirringthe mixture stirred for 15.5 h
  3. filtrationThe reaction mixture was filtered through celite-silica gel

Sources & evidence

ORD record
ord-a29d3ac0ac524067a123f579994d78b1
Source dataset
uspto-grants-2015_12
Patent number
US09206122B2

Reaction notes

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