HCID 86683898, compound → HCID 86683897, compound

HRID 340519Notes

Reaction equation

HRID 340519 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[C:17]([F:18])=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:19][C:20]2[CH:21]=[C:22]3[C:27](=[C:28]([O:30]CC4C=CC=CC=4)[CH:29]=2)[N:26]=[CH:25][CH:24]=[CH:23]3)[N:10]=1>[OH-].[OH-].[Pd+2].CO>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[C:17]([F:18])=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:19][C:20]2[CH:21]=[C:22]3[C:27](=[C:28]([OH:30])[CH:29]=2)[N:26]=[CH:25][CH:24]=[CH:23]3)[N:10]=1

Participants

4

Reactant 1

HCID 86683898HCID 86683898, compound

Product 1

HCID 86683897HCID 86683897, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A methanol (5 ml) solution containing 6-(((cis)-2-aminocyclohexyl)amino)-2-((8-(benzyloxy)quinolin-6-yl)amino)-5-fluoronicotinamide (20 mg) was prepared and was subjected to a hydrogenation reaction (room temperature; 1 bar; flow rate: 1 ml/min; 20% Pd(OH)2/C) using H-cube™. Then, the solvent was distilled away under reduced pressure. The residue was dissolved in ethyl acetate, 4M hydrogen chloride/1,4-dioxane (50 μl) was added, the resulting precipitate was collected by filtration, and a yellow solid of 6-(((cis)-2-aminocyclohexyl)amino)-5-fluoro-2-((8-hydroxyquinolin-6-yl)amino)nicotinamide (12 mg) was thus obtained.

Workup

  1. customwas prepared
  2. distillationThen, the solvent was distilled away under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. addition4M hydrogen chloride/1,4-dioxane (50 μl) was added
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f1fb4223409741249ca8e80d781e72e3
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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