HCID 53853654, compound → HCID 22615093, compound

HRID 843181Notes

Reaction equation

HRID 843181 reaction equation
C(OC(=O)[N:7]([CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:24]2[C:25]([CH3:36])=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[O:27][C:23]=2[CH:22]=[CH:21][CH:20]=1)[CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:35][O:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:26]1[O:27][C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([O:18][CH2:17][CH2:16][CH2:15][NH:7][CH2:8][C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[C:24]=2[C:25]=1[CH3:36]

Participants

4

Reactant 1

HCID 53853654HCID 53853654, compound

Product 1

HCID 22615093HCID 22615093, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

{3-[2-(2-Methoxy-phenyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-carbamic acid tert-butyl ester (24 mg) was treated in 10% trifluoroacetic acid in dichloromethane at room temperature for 18 hours. The mixture was washed with saturated sodium bicarbonate solution and the organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the residue was purified by silica gel TLC (dichloromethane-methanol=10:1) to give a pale yellow oil (17 mg, 88%). FAB-MS: m/z 402 (MH+); 1H-NMR (CDCl3) δ: 2.07 (2H, tt, J=6.6 Hz, 5.9 Hz), 2.28 (3H, s), 2.90 (2H, t, 6.6 Hz), 3.84 (3H, s), 3.85 (2H, s), 4.17 (2H, t, J=5.9 Hz), 6.61 (1H, d, J=7.6 Hz), 6.95-7.23 (5H, m), 7.40 (1H, dt, J=7.6 Hz, 1.7 Hz), 7.46 (1H, dd, J=7.6, 1.7 Hz), 7.67 (1H, d, J=7.4 Hz), 8.48 (1H, d, J=3.0 Hz), 8.56 (1H, s).

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate solution
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel TLC (dichloromethane-methanol=10:1)

Sources & evidence

ORD record
ord-80dfa2f0f04940cfbd7ed6b36006502a
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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