3-[4-(benzyloxy)-2-methoxyphenyl]-4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole → HCID 135434014, compound

HRID 22828Notes

Reaction equation

HRID 22828 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH3:20])[C:18]([C:21]34[CH2:28][CH2:27][C:24]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH2:25][CH2:26]3)[CH2:23][CH2:22]4)=[N:17][N:16]=2)=[C:11]([O:34][CH3:35])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:35][O:34][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[C:15]1[N:19]([CH3:20])[C:18]([C:21]23[CH2:26][CH2:25][C:24]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH2:27][CH2:28]2)[CH2:23][CH2:22]3)=[N:17][N:16]=1

Participants

4

Reactant 1

HCID 117546303-[4-(benzyloxy)-2-methoxyphenyl]-4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole

Product 1

HCID 135434014HCID 135434014, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-[4-(benzyloxy)-2-methoxyphenyl]-4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole (1-E) (272 mg, 0.572 mmol) in MeOH (8 mL) was hydrogenated for 19 h with 10% Pd/C catalyst (27 mg) at room temperature and atmospheric pressure. The catalyst was filtered and washed with MeOH. The MeOH was removed in vacuo to afford 3-methoxy-4-[4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazol-3-yl]phenol (1-F). MS: m/z 384 (M+1); 1H NMR (500 MHz, DMSO-d6): δ 9.94 (s 1H), 7.09 (d, 1H, J=8.3), 6.53 (d, 1H, J=1.6 Hz), 6.46 (dd, 1H, J=2.2, 8.2 Hz), 3.72 (s, 3H), 3.40 (s, 3H), 1.95 (m, 6H), 1.44 (m, 6H), 1.07-1.33 (m, 8H), 0.86 (t, 3H, J=7.2).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with MeOH
  3. customThe MeOH was removed in vacuo

Sources & evidence

ORD record
ord-0e262b181dbd43ebbb92b98d63586004
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

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