Trifluoroacetic acid → HCID 53237106, compound

HRID 407191Notes

Reaction equation

HRID 407191 reaction equation
[C:1]([C:3]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([C:21]([NH:23][CH:24]3[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)=[O:22])[C:13](=[O:20])[N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH2:5][CH2:4]1)#[N:2].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:3]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[CH2:4][CH2:5][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([C:21]([NH:23][CH:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)=[O:22])[C:13](=[O:20])[N:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86670624HCID 86670624, compound

Product 1

HCID 53237106HCID 53237106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[({1-[(4-cyano-4-pyridin-2-ylpiperidin-1-yl)methyl]-4-oxo-4H-quinolizin-3-yl}carbonyl)amino]piperidine-1-carboxylate (0.335 g, 0.587 mmol) in 12 mL of dichloromethane at 0° C. was added trifluoroacetic acid (1.17 mL, 15.2 mmol). The mixture was warmed to rt, and after 2 h, treated with saturated aqueous sodium bicarbonate and extracted 3× with dichloromethane. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title compound that gave a proton NMR spectra consistent with theory and a high resolution mass spectrum (ES+) m/z of 471.2504 calculated for M+H+ [C27H31N6O2: 471.2503]: 1H NMR (400 MHz, CDCl3) δ 9.93 (d, J=7.5 Hz, 1H), 9.38 (d, J=7.3 Hz, 1H), 8.60 (s, 1H), 8.55 (d, J=4.0 Hz, 1H), 8.14 (d, J=9.0 Hz, 1H), 7.71-7.61 (m, 2H), 7.56 (d, J=8.0 Hz, 1H), 7.27-7.19 (m, 2H), 4.21-4.18 (m, 1H), 3.78 (s, 2H), 3.30-3.27 (m, 1H), 3.00-2.76 (m, 4H), 2.63-2.53 (m, 3H), 2.29-2.21 (m, 2H), 2.05-1.86 (m, 3H), 1.85 (br s, 1H), 1.70-1.53 (m, 2H).

Workup

  1. extractionextracted 3× with dichloromethane
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08cf6d4b4c394928bf836c7bf828c7f5
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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