Trifluoroacetic acid → HCID 68288226, compound

HRID 541194Notes

Reaction equation

HRID 541194 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:18]([CH3:40])=[CH:19][C:20]([CH3:39])=[C:21]([C:23]4[NH:38][C:26]5[CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][CH2:30][C:25]=5[N:24]=4)[CH:22]=3)=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[CH3:40][C:18]1[CH:19]=[C:20]([CH3:39])[C:21]([C:23]2[NH:38][C:26]3[CH2:27][NH:28][CH2:29][CH2:30][C:25]=3[N:24]=2)=[CH:22][C:17]=1[C:15]([N:12]1[CH2:11][CH2:10][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[CH2:14][CH2:13]1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68288848HCID 68288848, compound2×

Product 1

HCID 68288226HCID 68288226, compoundYield 133.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2,4-dimethylphenyl)-6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate (compound 2.8, 100 mg, 0.17 mmol, 1.00 equiv, 90%) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL). The resulting mixture was stirred at room temperature. After 2 h, the reaction mixture was concentrated under reduced pressure. The residue was taken up in dichloromethane and washed with sodium bicarbonate (aq., sat.). The organic phase was dried (Na2SO4) and concentrated under reduced pressure to yield 0.1 g (68%) of the title compound as a yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. washwashed with sodium bicarbonate (aq., sat.)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44fc79dafe5145188a16af376021f070
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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