Acetic Acid → HCID 87158590, compound

HRID 2206910Notes

Reaction equation

HRID 2206910 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:13])[CH2:11][CH3:12])=[CH:6][CH:5]=[C:4]([N:14]2[CH2:18][CH2:17][C:16]([C:23]3[CH:28]=[C:27]([Cl:29])[C:26]([Cl:30])=[C:25]([Cl:31])[CH:24]=3)([C:19]([F:22])([F:21])[F:20])[CH2:15]2)[N:3]=1.ClCCl.C(O)(=[O:37])C>[O-2].[O-2].[Mn+4]>[OH:37][CH:15]1[C:16]([C:23]2[CH:24]=[C:25]([Cl:31])[C:26]([Cl:30])=[C:27]([Cl:29])[CH:28]=2)([C:19]([F:22])([F:20])[F:21])[CH2:17][CH2:18][N:14]1[C:4]1[N:3]=[C:2]([CH3:1])[C:7]([CH2:8][NH:9][C:10](=[O:13])[CH2:11][CH3:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 87158483HCID 87158483, compound

Product 1

HCID 87158590HCID 87158590, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

N-({2-Methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-pyridin-3-yl}-methyl)propanamide (0.15 g) and manganese dioxide (1.2 g) were added to dichloromethane (20 ml), and acetic acid (2 ml) was added thereto in small portions at room temperature. The reaction mixture was stirred for 100 hours at room temperature, and filtered by suction on Celite. The filtrate was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain N-({6-[2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-methylpyridin-3-yl}methyl)propanamide (0.06 g).

Workup

  1. additionwas added
  2. customat room temperature
  3. filtrationfiltered by suction on Celite
  4. distillationThe filtrate was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-81085d85e00f4a02ae1a1a9f33ed9fbc
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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