Hydrazine → HCID 178428215, compound

HRID 2283504Notes

Reaction equation

HRID 2283504 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[N:5]=[C:4]([C:19]2[CH:20]=[N:21][C:22]([C:25]([CH:27]3[CH2:32][CH2:31][CH:30]([C:33]([O:35]C)=[O:34])[CH2:29][CH2:28]3)=O)=[CH:23][CH:24]=2)[CH:3]=1.[OH-].[K+].NN>CS(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[CH:12]=[CH:11][N:10]=2)[N:5]=[C:4]([C:19]2[CH:20]=[N:21][C:22]([CH2:25][C@H:27]3[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]3)=[CH:23][CH:24]=2)[CH:3]=1.[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[CH:12]=[CH:11][N:10]=2)[N:5]=[C:4]([C:19]2[CH:20]=[N:21][C:22]([CH2:25][C@@H:27]3[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]3)=[CH:23][CH:24]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 70983105HCID 70983105, compound

Product 2

HCID 178428215HCID 178428215, compoundHCID 178428216HCID 178428216, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a flask containing methyl 4-[(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)carbonyl]cyclohexanecarboxylate (50 mg, 0.10 mmol) in DMSO (1 mL) was added potassium hydroxide (113 mg, 2.01 mmol) and hydrazine (57 μL, 1.81 mmol). The reaction was heated in a sealed vessel to 140° C. for 3 hours. The reaction mixture was then cooled to ambient temperature and filtered. The solution was then purified directly by reverse phase column chromatography (acetonitrile/water with 0.1% TFA modifier) to afford trans-4-[(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)methyl]cyclohexanecarboxylic acid and cis-4-[(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)methyl]cyclohexanecarboxylic acid.

Workup

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. filtrationfiltered
  3. customThe solution was then purified directly by reverse phase column chromatography (acetonitrile/water with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-44fe35adb95048b1afa174901b36d3be
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

Loading…