Ammonium Chloride → N-[1-(2-phenylethyl)-4-ethoxycarbonyl-5-bromopyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine

HRID 863710Notes

Reaction equation

HRID 863710 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC.[C:17]1([CH2:23][CH2:24][N:25]2[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:27]([N:35]([CH2:73][CH2:74][CH3:75])[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]4[N:53]([C:54]([C:67]5[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=5)([C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)[C:55]5[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=5)[N:52]=[N:51][N:50]=4)=[CH:39][CH:38]=3)=[N:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Br:76]C(F)(F)C(Br)(F)F.[Cl-].[NH4+]>C1COCC1.CN1CCCN(C)C1=O>[C:17]1([CH2:23][CH2:24][N:25]2[C:29]([Br:76])=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:27]([N:35]([CH2:73][CH2:74][CH3:75])[CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]4[N:53]([C:54]([C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)([C:61]5[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=5)[C:55]5[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=5)[N:52]=[N:51][N:50]=4)=[CH:39][CH:38]=3)=[N:26]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 22103832N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamineHCID 86588928Lithium bis(trimethylsilyl)amide hexane

Product 1

HCID 22103828N-[1-(2-phenylethyl)-4-ethoxycarbonyl-5-bromopyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

1.52 ml of 1.0M lithium bis(trimethylsilyl)amide/hexane solution were added to THF solution (20 ml) containing 395 mg of N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine and 0.18 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, at room temperature, and then heated under reflux for 30 minutes. 0.60 ml of 1,2-dibromo-1,1,2,2-tetrafluoroethane was added thereto and heated under reflux for further 30 minutes. 10 ml of ammonium chloride were added to the reaction solution, THF was distilled off under reduced pressure, and the resultant was extracted with 150 ml of dichloromethane. The resulting extract was dried over magnesium sulfate and subjected to silica gel column chromatography (n-hexane-ethyl acetate=2:1) to obtain 363 mg of the intended compound as a pale red, amorphous solid.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureheated
  3. temperatureunder reflux for further 30 minutes
  4. distillationwas distilled off under reduced pressure
  5. extractionthe resultant was extracted with 150 ml of dichloromethane
  6. extractionThe resulting extract
  7. dry with materialwas dried over magnesium sulfate

Sources & evidence

ORD record
ord-2a1f4b46534249499207ee6682ff8d9d
Source dataset
uspto-grants-1998_02
Patent number
US05721264

Reaction notes

Loading…