HCID 178468538, compound → HCID 178468537, compound

HRID 336846Notes

Reaction equation

HRID 336846 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[F:39])[NH:23][C:22]4[NH:40][N:41]=[C:42]([CH3:43])[C:21]3=4)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>ClCCl.[O-2].[Mn+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([C:31]4[C:36]([F:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=4[F:39])[N:23]=[C:22]4[NH:40][N:41]=[C:42]([CH3:43])[C:21]=34)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178468538HCID 178468538, compound

Product 1

HCID 178468537HCID 178468537, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2.2 g (3.68 mmol) of ethyl 4-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-3-methyl-6-(2,3,6-trifluorophenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in solution in 50 ml of dichloromethane are added 1.6 g (18.41 mmol) of manganese oxide. The reaction mixture is sonicated for 5 min then stirred at room temperature for 20 h. It is filtered on silica (cyclohexane/ethyl acetate eluent: 6:4) to yield 2 g (91%) of ethyl 4-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-3-methyl-6-(2,3,6-trifluorophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in the form of a yellow solid.

Workup

  1. customThe reaction mixture is sonicated for 5 min
  2. filtrationIt is filtered on silica (cyclohexane/ethyl acetate eluent: 6:4)

Sources & evidence

ORD record
ord-024ebdfe2aeb4373b1235b55df052c0e
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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