Ammonia → HCID 22615025, compound

HRID 843175Notes

Reaction equation

HRID 843175 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[O:11][C:12]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[C:13]=3[C:14]=2[CH3:15])=[CH:4][CH:3]=1.[OH:32]O.N>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:9][C:10]2[O:11][C:12]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[C:13]=3[C:14]=2[CH3:15])=[O:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 22615087HCID 22615087, compound

Product 1

HCID 22615025HCID 22615025, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-[2-(4-fluoro-phenylsulfanylmethyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-amine (16 mg) and bis(2,4-pentanedionato)-vanadium oxide (9.8 mg) in dichloromethane (2 ml) was added 30% hydrogenperoxide aqueous solution (20 μl) at room temperature and the mixture was stirred for 1 hour. After the addition of ammonia solution (2 ml) the whole mixture was vigorously stirred until the sticky precipitation disappeared, then extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. The mixture was separated by silica gel column chromatography developed by dichloromethane and methanol. {3-[2-(4-fluoro-benzenesulfinylmethyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-amine (5 mg) was obtained as a white solid: ESI-MS: m/z 453 (MH+); 1H-NMR (CDCl3): δ 1.98 (3H, s), 2.00-2.09 (2H, m), 2.85 (2H, t, J=6.9 Hz), 4.01 (1H, d, J=13.5 Hz), 4.13 (2H, t, J=5.9 Hz), 4.32 (1H, d, J=13.5 Hz), 6.59 (1H, d, J=7.9 Hz), 6.94 (1H, d, J=8.2 Hz), 7.10-7.25 (4H, m), 7.44-7.49 (2H, m), 7.65-7.69 (1H, m), 8.49-8.59 (2H, m). {3-[2-(4-fluoro-benzenesulfonylmethyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-amine (11 mg) was obtained as a colorless oil:. ESI-MS: m/z 469 (MH+); 1H-NMR (CDCl3): δ 1.99-2.09 (2H, m), 2.12 (3H, s), 2.86 (2H, t, J=7.3 Hz), 3.84 (2H, s), 4.13 (2H, t, J=5.9 Hz), 4.50 (2H, s), 6.59 (1H, d, J=8.3 Hz), 6.89 (1H, d, J=8.2 Hz), 7.11-7.69 (7H, m), 7.69-8.57 (2H, m).

Workup

  1. stirringwas vigorously stirred until the sticky precipitation
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe mixture was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-4a42945a15584535a62c84aedeb62720
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

Loading…