HCID 86683898, compound → HCID 86683897, compound

HRID 1620126Notes

Reaction equation

HRID 1620126 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-84a52b1b622c463bb76be2749b025c52
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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