tert-butyl 4-[4-[5-cyano-3-methyl-6-(2,3,6-trifluorophenyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridin-4-yl]phenyl]piperazine-1-carboxylate → HCID 178434431, compound

HRID 336845Notes

Reaction equation

HRID 336845 reaction equation
[C:1]([C:3]1[CH:4]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[C:5]2[C:20]([CH3:21])=[N:19][NH:18][C:6]=2[NH:7][C:8]=1[C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=1[F:17])#[N:2]>ClCCl.[O-2].[Mn+2]>[C:1]([C:3]1[C:4]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]3)=[CH:24][CH:23]=2)=[C:5]2[C:20]([CH3:21])=[N:19][NH:18][C:6]2=[N:7][C:8]=1[C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:10]=1[F:17])#[N:2]

Participants

4

Reactant 1

HCID 178434166tert-butyl 4-[4-[5-cyano-3-methyl-6-(2,3,6-trifluorophenyl)-2,4-dihydro-1H-pyrazolo[3,4-b]pyridin-4-yl]phenyl]piperazine-1-carboxylate

Product 1

HCID 178434431HCID 178434431, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2.48 g (4.50 mmol) of tert-butyl 4-(4-(5-cyano-3-methyl-6-(2,3,6-trifluorophenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)piperazine-1-carboxylate diluted in 20 ml of dichloromethane are added 1.96 g (22.5 mmol) of manganese oxide. The reaction mixture is sonicated for 5 min then stirred at room temperature for 18 h. It is next filtered on Celite (cyclohexane/ethyl acetate eluent: 5:5) to yield 1.86 g of tert-butyl 4-(4-(5-cyano-3-methyl-6-(2,3,6-trifluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)piperazine-1-carboxylate in the form of a light yellow solid.

Workup

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

Sources & evidence

ORD record
ord-d680c467feb6481fac57fd2d5c4750fd
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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