Hydrochloric Acid → HCID 178446408, compound

HRID 492296Notes

Reaction equation

HRID 492296 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([CH2:16][N:17]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[N:35](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:34]=[N:33][N:32]=2)=[CH:21][CH:20]=1)=[O:15])([CH3:3])[CH3:2].[ClH:60]>O1CCCC1>[ClH:60].[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:13][C:14]([CH2:16][N:17]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:35][N:34]=[N:33][N:32]=2)=[CH:21][CH:20]=1)=[O:15])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68853185N-[[[(2,6-diisopropylphenyl)amino]carbonyl]methyl]-N-pentyl-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amine

Product 1

HCID 178446408HCID 178446408, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[[[(2,6-Diisopropylphenyl)amino]carbonyl]methyl]-N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (278.3 mg) was dissolved in tetrahydrofuran (10 mL), and after addition of 10% hydrochloric acid (3.0 mL), the resulting mixture was stirred at room temperature. Nineteen hours later, the solvent was distilled off, and to the residue, water (30 mL) was added. The mixture so obtained was extracted twice with chloroform (30 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 (chloroform/methanol) to afford N-[[[(2,6-diisopropylphenyl) amino]carbonyl]methyl]-N-pentyl-N-[[2′-(1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl]amine hydrochloride as pale yellow crystals (190.6 mg). Yield: 93%.

Workup

  1. distillationNineteen hours later, the solvent was distilled off
  2. additionto the residue, water (30 mL) was added
  3. customThe mixture so obtained
  4. extractionwas extracted twice with chloroform (30 mL
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7c89b6497a54b7c91d01de2b632be69
Source dataset
uspto-grants-2009_05
Patent number
US07531576B2

Reaction notes

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