Sodium Bicarbonate → N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine

HRID 473710Notes

Reaction equation

HRID 473710 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][N:14]=2)[CH2:5][CH2:4]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH:3]1[CH2:4][CH2:5][CH:6]([C:9]2[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][N:14]=2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67425394N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine dihydrochloride

Product 1

HCID 59373943N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine dihydrochloride (218 mg, 0.519 mmol) and DCM (20 mL) was added sat'd NaHCO3 (7 mL). The organic layer was eluted through a Redi-Sep® pre-packed silica gel column (4 g), with 15% MeOH in DCM, to provide N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine as an off-white foam. MS (ESI, pos. ion) m/z: 348.2 (M+1). IC50 (uM) 0.2215.

Workup

  1. washThe organic layer was eluted through a Redi-Sep® pre-packed silica gel column (4 g), with 15% MeOH in DCM

Sources & evidence

ORD record
ord-f576bed0649249919d193cc309e82a9a
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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