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

HRID 1623263Notes

Reaction equation

HRID 1623263 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-ac446343310b4e018e85d5af950cf1a5
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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