Trifluoroacetic acid → 6-((3-methylpiperazin-1-yl)methyl)nicotinonitrile TFA salt

HRID 874939Notes

Reaction equation

HRID 874939 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH:19]([CH3:30])[CH2:18]2)=[N:14][CH:15]=1)#[N:9]>C(Cl)Cl>[OH:5][C:3]([C:2]([F:7])([F:6])[F:1])=[O:4].[CH3:30][CH:19]1[NH:20][CH2:21][CH2:22][N:17]([CH2:16][C:13]2[CH:12]=[CH:11][C:10]([C:8]#[N:9])=[CH:15][N:14]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69935268Tert-butyl 4-((5-cyanopyridin-2-yl)methyl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 866735316-((3-methylpiperazin-1-yl)methyl)nicotinonitrile TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.8 mL) was added dropwise to the cold solution of tert-butyl 4-((5-cyanopyridin-2-yl)methyl)-2-methylpiperazine-1-carboxylate (200 mg, 0.63 mmol) in CH2Cl2 (3 mL) at 0° C. and the reaction mixture was further stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure to afford 6-((3-methylpiperazin-1-yl)methyl)nicotinonitrile TFA salt (180 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C12H16N4: 216.14. found: 217.0 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4a1a5d9ddc384c719aa2fad0b657830b
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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