Cesium carbonate → N-(4-(3-chloropyrazin-2-yloxy)phenyl)pyridin-2-amine

HRID 473616Notes

Reaction equation

HRID 473616 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Cl:15][C:16]1[C:21](Cl)=[N:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:15][C:16]1[C:21]([O:14][C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:9][CH:10]=2)=[N:20][CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 785752,3-DichloropyrazineHCID 212625714-(Pyridin-2-ylamino)phenol

Product 1

HCID 53485989N-(4-(3-chloropyrazin-2-yloxy)phenyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(pyridin-2-ylamino)phenol (14.551 g, 78.14 mmol) and 2,3-dichloropyrazine (11.64 g, 78.14 mmol) in DMSO was added CESIUM CARBONATE (30.55 g, 93.77 mmol). The resulting mixture was heated to 60° C. overnight. Aqueous workup was carried out with DCM extraction and washing with alternating water and brine solutions. Purification by Biotage (0-2%, then 2% MeOH/DCM), followed by washing with EtOAc, produced clean product as solid. MS (ESI, pos. ion) m/z: 298.8 (M+1). IC50 (uM) 0.475.

Workup

  1. extractionAqueous workup was carried out with DCM extraction
  2. washwashing with alternating water and brine solutions
  3. customPurification by Biotage (0-2%
  4. washby washing with EtOAc
  5. customproduced clean product as solid

Sources & evidence

ORD record
ord-0fff887d9f114967acff7406460d3c46
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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