Butylamine → N-[1-(2-phenylethyl)-5-(n-butylamino)-4-ethoxycarbonyl-pyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine

HRID 863714Notes

Reaction equation

HRID 863714 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH2:11])[CH2:8][CH2:9][CH3:10].[C:12]1([CH2:18][CH2:19][N:20]2[C:24](Br)=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]([N:31]([CH2:69][CH2:70][CH3:71])[CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[C:45]4[N:49]([C:50]([C:63]5[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=5)([C:57]5[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=5)[C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)[N:48]=[N:47][N:46]=4)=[CH:35][CH:34]=3)=[N:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Cu]=O>[C:12]1([CH2:18][CH2:19][N:20]2[C:24]([NH:11][CH2:7][CH2:8][CH2:9][CH3:10])=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]([N:31]([CH2:69][CH2:70][CH3:71])[CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[C:45]4[N:49]([C:50]([C:63]5[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=5)([C:57]5[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=5)[C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)[N:48]=[N:47][N:46]=4)=[CH:35][CH:34]=3)=[N:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 22103828N-[1-(2-phenylethyl)-4-ethoxycarbonyl-5-bromopyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine

Product 1

HCID 22103830N-[1-(2-phenylethyl)-5-(n-butylamino)-4-ethoxycarbonyl-pyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine

Reagents, catalysts & solvents 1

HCID 14829Copper oxideCatalyst

Procedure

30 mg of reduced copper, 20 mg of copper(II) oxide, 83 mg of potassium carbonate and 5 ml of n-butylamine were added to 216 mg of N-[1-(2-phenylethyl)-5-bromo-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine, and heated under reflux for 14 hours. The reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane-ethyl acetate=7:1) to obtain 92 mg of the intended compound as a pale yellow, amorphous solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 14 hours
  3. filtrationThe reaction solution was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-abe6a780ec7c43289a88df633eeb6365
Source dataset
uspto-grants-1998_02
Patent number
US05721264

Reaction notes

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