N-[2-{1-[benzyl(methyl)amino]-propyl}-5-(trifluoromethyl)benzyl]-N-[3,5-bis(trifluoromethyl)-benzyl]-2-methyl-2H-tetrazol-5-amine → N-[3,5-bis(trifluoromethyl)benzyl]-2-methyl-N-{2-[1-(methyl-amino)propyl]-5-(trifluoromethyl)benzyl}-2H-tetrazol-5-amine

HRID 390745Notes

Reaction equation

HRID 390745 reaction equation
[CH2:1]([N:8](C)[CH:9]([C:12]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:13]=1[CH2:14][N:15]([CH2:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=1)[C:16]1[N:17]=[N:18][N:19]([CH3:21])[N:20]=1)[CH2:10][CH3:11])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:32][C:29]([F:30])([F:31])[C:27]1[CH:28]=[C:23]([CH:24]=[C:25]([C:33]([F:34])([F:35])[F:36])[CH:26]=1)[CH2:22][N:15]([CH2:14][C:13]1[CH:37]=[C:38]([C:41]([F:44])([F:43])[F:42])[CH:39]=[CH:40][C:12]=1[CH:9]([NH:8][CH3:1])[CH2:10][CH3:11])[C:16]1[N:17]=[N:18][N:19]([CH3:21])[N:20]=1

Participants

4

Reactant 1

HCID 58966437N-[2-{1-[benzyl(methyl)amino]-propyl}-5-(trifluoromethyl)benzyl]-N-[3,5-bis(trifluoromethyl)-benzyl]-2-methyl-2H-tetrazol-5-amine

Product 1

HCID 58966411N-[3,5-bis(trifluoromethyl)benzyl]-2-methyl-N-{2-[1-(methyl-amino)propyl]-5-(trifluoromethyl)benzyl}-2H-tetrazol-5-amineYield 109%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a Parr flask was added 20% Pd(OH)2 on carbon (23.2 mg) followed by addition of methanol (22 mL). To this suspension was added a solution N-[2-{1-[benzyl(methyl)amino]-propyl}-5-(trifluoromethyl)benzyl]-N-[3,5-bis(trifluoromethyl)-benzyl]-2-methyl-2H-tetrazol-5-amine (298.7 mg, 0.463 mmoles) in methanol. The reaction mixture was stirred under hydrogen (pressure =14.7 psi) at room temperature for 9 hours. The reaction mixture was filtered through Celite, washed with methanol, concentrated under vacuo to give 279.8 mg (100%) of the title compound as yellow oil. MS (ES+) Calc: 608.5, Found: 609.1 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with methanol
  3. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-e696dddc2e264a769428064a1ab4c03e
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Reaction notes

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