trans-1-{4-(Benzyl-methylamino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea → trans-1-{4-Methylamino-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea

HRID 896558Notes

Reaction equation

HRID 896558 reaction equation
[CH2:1]([N:8](C)[C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:11][C@H:10]1[CH2:24][NH:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([C:35]2[N:39]([CH3:40])[N:38]=[N:37][N:36]=2)[CH:32]=[C:31]([CH2:41][CH3:42])[CH:30]=1)=[O:27])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:1][NH:8][C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:11][C@H:10]1[CH2:24][NH:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([C:35]2[N:39]([CH3:40])[N:38]=[N:37][N:36]=2)[CH:32]=[C:31]([CH2:41][CH3:42])[CH:30]=1)=[O:27]

Participants

4

Reactant 1

HCID 10415913trans-1-{4-(Benzyl-methylamino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea

Product 1

HCID 10323481trans-1-{4-Methylamino-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-ureaYield 97.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of trans-1-{4-(benzyl-methylamino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea (95 mg, 162 μmol) in methanol (20 mL) was combined with Pearlman's catalyst (20% palladium hydroxide on charcoal, 100 mg) and shaken under a hydrogen atmosphere (60 psig) for 15 hours. The mixture was filtered through Celite and the solids were washed with methanol. The filtrate was concentrated under vacuum to provide a pale tan solid (78 mg, 97%). 1H NMR (300 MHz, CDCl3) δ7.78 (s, 1H), 7.36 (s, 1H), 7.16 (m, 2H), 7.13 (s, 1H), 6.96 (t, J=9 Hz, 2H), 4.14 (s, 3H), 3.66 (m, 1H), 3.4-3.1 (m, 4H), 2.95 (s, 3H), 2.9-2.3 (m, 12H), 2.18 (m, 2H), 1.22 (t, J=8 Hz, 3H). Mass spec (ES+) m/z 495.2 (M+H+).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed with methanol
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-826ebf62f92f4ad5b868ca5d08fd11ae
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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