Trifluoroacetic acid → HCID 72551158, compound

HRID 1057030Notes

Reaction equation

HRID 1057030 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:15]=[C:14]([CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[CH:13]=[C:12]([CH3:29])[N:11]=2)[CH:4]=1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:29][C:12]1[N:11]=[C:10]([NH:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][N:6]=2)[C:1]#[N:2])[CH:15]=[C:14]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72551155HCID 72551155, compound

Product 1

HCID 72551158HCID 72551158, compoundYield 138.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-((4-cyanopyridin-2-yl)amino)-6-methylpyridin-4-yl)piperidine-1-carboxylate (216 mg, 0.550 mmol) in CH2Cl2 (2.2 mL) was added trifluoroacetic acid (1.1 mL) and stirring was maintained for 2 hr. Concentrated to dryness afforded 2-((6-methyl-4-(piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile (1×TFA salt by 1H NMR) as a yellow solid (224 mg, >99%); 1H NMR (400 MHz, DMSO) δ 10.47 (br s, 1H), 8.65 (br s, 1H), 8.47 (d, J=5.1 Hz, 1H), 8.38 (br s, 1H), 8.07 (s, 1H), 7.36 (s, 1H), 7.32 (d, J=5.1 Hz, 1H), 6.80 (s, 1H), 3.40 (m, 2H), 3.02 (m, 2H), 2.93 (m, 1H), 2.47 (s, 3H), 1.96 (m, 2H), 1.76 (m, 2H); ESI-LRMS m/z [M+1]+=294.

Workup

  1. temperaturewas maintained for 2 hr
  2. concentrationConcentrated to dryness

Sources & evidence

ORD record
ord-a252a8c4fb6145fd9eebab100daa6b52
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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