Trifluoroacetic acid → 5'-chloro-2'-fluoro-N-((4-methoxytetrahydro-2H-pyran-4-yl)methyl)-2,4'-bipyridin-6-amine

HRID 1963843Notes

Reaction equation

HRID 1963843 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]([CH2:23][C:24]3([O:30][CH3:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)C(=O)OC(C)(C)C)[N:10]=2)=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:23][C:24]3([O:30][CH3:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:10]=2)=[CH:4][C:5]([F:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58127426tert-butyl 5'-chloro-2'-fluoro-2,4'-bipyridin-6-yl((4-methoxytetrahydro-2H-pyran-4-yl)methyl)carbamate

Product 1

HCID 581271875'-chloro-2'-fluoro-N-((4-methoxytetrahydro-2H-pyran-4-yl)methyl)-2,4'-bipyridin-6-amineYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 5′-chloro-2′-fluoro-2,4′-bipyridin-6-yl((4-methoxytetrahydro-2H-pyran-4-yl)methyl)carbamate (32 mg, 0.071 mmol) and TRIFLUOROACETIC ACID (0.982 ml, 12.75 mmol) in DCM (2 ml) was stirred at room temperature for 40 min. The mixture was then concentrated to afford 22 mg of the crude material which was used in the next step without purification. LCMS (m/z): 352.2 [M+H]+; Rt=0.634 min.

Workup

  1. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-13014994904041d6958b29b3ad97a7b4
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

Loading…