HCID 53876405, compound → HCID 500951, compound

HRID 843180Notes

Reaction equation

HRID 843180 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]([CH:28]([OH:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[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>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:36][C:25]1[C:24]2[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)=[CH:20][CH:21]=[CH:22][C:23]=2[O:27][C:26]=1[C:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=[O:35]

Participants

4

Reactant 1

HCID 53876405HCID 53876405, compound

Product 1

HCID 500951HCID 500951, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of {3-[2-(hydroxy-pyridin-2-yl-methyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-carbamic acid tert-butyl ester (30 mg) in chloroform (2 ml) was added manganese(IV) oxide (45 mg) at room temperature and the mixture was stirred vigorously overnight. The mixture was filtered through a pad of Celite and concentrated in vacuo. The titled compound (24 mg) was obtained as a pale yellow oil after the purification with silica gel TLC developed by the mixture of dichlormethane and methanol. FAB-MS: m/z 502 (MH+); 1H-NMR (CDCl3): δ 1.45 (9H, s), 2.10-2.15 (2H, m), 2.91 (3H, s), 3.40-3.50 (2H, m), 4.09 (2H, t, J=5.9 Hz), 4.48 (2H, broad s), 6.58 (1H, d, J=8.3 Hz), 7.10 (1H, d, J=8.3 Hz), 7.24 (1H, dd, J=5.3 Hz, 7.6 Hz), 7.34 (1H, t, J=8.3 Hz), 7.47-7.55 (2H, m), 7.87-7.98 (2H, m), 8.50-8.53 (2H, m), 8.77-8.80 (1H, m).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-746d8c49b6c047b8ba6161ee34854f4c
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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