Trifluoroacetic acid → HCID 68578141, compound

HRID 2047327Notes

Reaction equation

HRID 2047327 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:40])[NH:10][CH2:11][CH2:12][O:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([C:21]2[N:25]=[C:24]([C:26]3[CH:31]=[C:30]([CH3:32])[N:29]=[C:28]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH:27]=3)[O:23][N:22]=2)=[CH:16][C:15]=1[CH2:38][CH3:39])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CC(=O)OCC>[NH2:7][CH2:8][C:9]([NH:10][CH2:11][CH2:12][O:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([C:21]2[N:25]=[C:24]([C:26]3[CH:31]=[C:30]([CH3:32])[N:29]=[C:28]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH:27]=3)[O:23][N:22]=2)=[CH:16][C:15]=1[CH2:38][CH3:39])=[O:40]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68578029HCID 68578029, compound

Product 1

HCID 68578141HCID 68578141, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [(2-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethylcarbamoyl)-methyl]-carbamic acid tert-butyl ester (65 mg, 0.115 mmol) in DCM (30 mL), trifluoroacetic acid (262 mg, 2.29 mmol) is added. The mixture is stirred at rt for 16 h before it is diluted with EA and washed with sat. aq. NaHCO3-solution and brine. The org. extract is dried over Na2SO4, filtered and concentrated. The crude product is purified on prep. TLC plates using DCM containing 10% of 7 N NH3 in methanol to give the title compound (32 mg) as a yellow resin; LC-MS: tR=0.70 min; [M+1]+=467.19; 1H NMR (CDCl3): δ 1.24 (t, J=7.0 Hz, 6H), 1.32 (t, J=7.5 Hz, 3H), 2.01 (s br, 2H), 2.39 (s, 3H), 2.49 (s, 3H), 2.76 (q, J=7.5 Hz, 2H), 3.45 (s, 2H), 3.62 (q, J=7.0 Hz, 4H), 3.73-3.80 (m, 2H), 3.95 (t, J=5.0 Hz, 2H), 7.00 (s, 1H), 7.10 (s, 1H), 7.87 (s, 1H), 7.88 (s, 1H), 7.90 (s br, 1H).

Workup

  1. washwashed with sat. aq. NaHCO3-solution and brine
  2. extractionextract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-a77a27ac40dd460d8af05dfee092cef5
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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