Ammonium Chloride → N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl) methyl]amine

HRID 1457481Notes

Reaction equation

HRID 1457481 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH2:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1([CH2:21][CH2:22][N:23]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:25]([NH2:33])=[N:24]2)C=CC=CC=1.C(=O)=O.CC(C)=O.Br[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[C:55]2[N:59]([C:60]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[N:58]=[N:57][N:56]=2)=[CH:45][CH:44]=1.[Cl-].[NH4+]>CCCCCC.C(OCC)(=O)C.C1COCC1.CN1CCCN(C)C1=O>[C:9]1([CH2:21][CH2:22][N:23]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:25]([NH:33][CH2:42][C:43]3[CH:44]=[CH:45][C:46]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=4[C:55]4[N:59]([C:60]([C:73]5[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=5)([C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)[C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)[N:58]=[N:57][N:56]=4)=[CH:47][CH:48]=3)=[N:24]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 5

HCID 25517Ammonium ChlorideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 18522661Acetone cardice2×HCID 221038291-(2-Phenylethyl)-3-amino-4-ethoxycarbonylpyrazoleHCID 86604122LDA cyclohexane

Product 1

HCID 67637880N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl) methyl]amine

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-SolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

2.1 ml of 1.5 M lithium diisopropylamide/cyclohexane solution were added to THF solution (35 ml) containing 363 mg of 1-(2-phenylethyl)-3-amino-4-ethoxycarbonylpyrazole and 0.40 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, while cooling with dry ice-acetone, and stirred at room temperature for 15 minutes. The mixture was again cooled with dry ice-acetone, and 10 ml of THF solution of 877 mg of 4-bromomethyl-2'-[N-triphenylmethyl-(1H-tetrazol-5-yl)]biphenyl were added thereto and stirred at room temperature for 5.5 hours. 10 ml of aqueous ammonium chloride solution was added to the reaction solution, THF was distilled off under reduced pressure, and the resultant was extracted with 50 ml of dichloromethane. The resulting extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (n-hexane-ethyl acetate=3:1→2:1) to obtain 234 mg of the intended compound as a pale yellow, amorphous solid.

Workup

  1. additionwere added
  2. stirringstirred at room temperature for 5.5 hours
  3. distillationwas distilled off under reduced pressure
  4. extractionthe resultant was extracted with 50 ml of dichloromethane
  5. extractionThe resulting extract
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-ec5bf6aa4485450c84321071708b3250
Source dataset
uspto-grants-1998_12
Patent number
US05846991

Reaction notes

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