Trifluoroacetic acid → HCID 10022342, compound

HRID 1791365Notes

Reaction equation

HRID 1791365 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[N:18]=[C:17]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([C:27]#[N:28])[CH:20]=2)[O:16][N:15]=1)=O)(C)(C)C.F[C:30](F)(F)[C:31](O)=O>ClCCl>[CH3:26][O:25][C:23]1[CH:22]=[C:21]([CH:20]=[C:19]([C:17]2[O:16][N:15]=[C:14]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][N:8]3[CH2:6][C:31]3[CH:30]=[CH:11][CH:10]=[CH:9][N:8]=3)[N:18]=2)[CH:24]=1)[C:27]#[N:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10022903HCID 10022903, compound

Product 1

HCID 10022342HCID 10022342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[5-(3-cyano-5-methoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester (162 mg, 0.42 mmol) in dichloromethane (4 mL) cooling in an ice-bath was added trifluoroacetic acid (2 mL). The ice-bath was removed after 30 min. and then left stirring for an additional hour. After the solvent was removed in vacuo, the residue was dissolved in ethyl acetate and then washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo 113 mg (94%) of the title compound as a white solid. 1H NMR (CDCl3), δ(ppm): 7.99 (s, 1H), 7.84 (d, 1H), 7.35 (s, 1H), 5.56 (bs, 1H), 4.06 (m 1H), 3.93 (s, 3H), 3.01 (m, 1H), 2.84 (m, 1H), 1.92 (m, 1H), 1.70 (m, 2H), 1.49 (m 1H).

Workup

  1. customThe ice-bath was removed after 30 min.
  2. waitleft
  3. customAfter the solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo 113 mg (94%) of the title compound as a white solid

Sources & evidence

ORD record
ord-dbd37b52b58d4dac829cc80eb1f6e6a3
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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