HCID 178434381, compound → HCID 178434379, compound

HRID 336853Notes

Reaction equation

HRID 336853 reaction equation
[C:1]([C:3]1[C:4]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]3)=[CH:25][CH:24]=2)=[C:5]2[C:21]([CH3:22])=[N:20][NH:19][C:6]2=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[F:18])#[N:2]>C(O)C.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[N:7]=[C:6]3[NH:19][N:20]=[C:21]([CH3:22])[C:5]3=[C:4]([C:23]3[CH:24]=[CH:25][C:26]([N:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[CH:27][CH:28]=3)[C:3]=2[C:1]#[N:2])=[C:10]([F:18])[CH:11]=1

Participants

4

Reactant 1

HCID 178434381HCID 178434381, compound

Product 1

HCID 178434379HCID 178434379, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.15 g (0.27 mmol) of tert-butyl 4-(4-(5-cyano-6-(2-fluoro-4-nitrophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)piperazine-1-carboxylate in 15 ml of ethanol are added 0.037 g (0.035 mmol) of 10% Pd/C. The mixture is stirred at room temperature for 18 h under hydrogen atmospheric pressure. The mixture is then concentrated, re-dissolved in dichloromethane, filtered through Celite, and concentrated. The residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 0 to 5%) to yield 0.020 g (14%) of tert-butyl 4-(4-(6-(4-amino-2-fluorophenyl)-5-cyano-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)piperazine-1-carboxylate in the form of yellow crystals.

Workup

  1. concentrationThe mixture is then concentrated
  2. dissolutionre-dissolved in dichloromethane
  3. filtrationfiltered through Celite
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 0 to 5%)

Sources & evidence

ORD record
ord-37a5aa8ff35340519d985e620c26ec48
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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