Potassium Iodide → N-pentyl-N-[[[(2,4,6-trifluorophenyl)amino]carbonyl]methyl]-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amine

HRID 492298Notes

Reaction equation

HRID 492298 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][C:7]=1[F:14])=[O:4].[CH2:15]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[N:38]([C:39]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:37]=[N:36][N:35]=2)=[CH:24][CH:23]=1)[CH2:16][CH2:17][CH2:18][CH3:19].[I-].[K+].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH2:15]([N:20]([CH2:2][C:3]([NH:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][C:7]=1[F:14])=[O:4])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[N:38]([C:39]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[N:37]=[N:36][N:35]=2)=[CH:26][CH:27]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 17860717N-(Chloroacetyl)-2,4,6-trifluoroanilineHCID 19024425pentyl[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]amine

Product 1

HCID 68851372N-pentyl-N-[[[(2,4,6-trifluorophenyl)amino]carbonyl]methyl]-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amineYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N-(Chloroacetyl)-2,4,6-trifluoroaniline (313.0 mg), N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (780.0 mg), potassium iodide (230 mg) and triethylamine (2.1 g) were suspended in dimethylformamide (12 mL). The resulting mixture was heated to about 80° C., and then stirred at that temperature. Three hours later, the reaction mixture was cooled, ethyl acetate (100 mL) was added, and the mixture was washed four times with brine (200 mL, each). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane/ethyl acetate) to afford N-pentyl-N-[[[(2,4,6-trifluorophenyl)amino]carbonyl]methyl]-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (434.8 mg). Yield: 42%.

Workup

  1. temperatureThree hours later, the reaction mixture was cooled
  2. washthe mixture was washed four times with brine (200 mL
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6480fe6c481d4d6e84613486eab1f95e
Source dataset
uspto-grants-2009_05
Patent number
US07531576B2

Reaction notes

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