HCID 15222072, compound → HCID 178440121, compound

HRID 274817Notes

Reaction equation

HRID 274817 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([CH2:47][CH2:48][CH3:49])=[N:7][C:6]=1[CH2:50][N:51]1[CH2:56][CH2:55][N:54]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)[CH2:53][CH2:52]1)=[O:4]>CO>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([CH2:47][CH2:48][CH3:49])=[N:7][C:6]=1[CH2:50][N:51]1[CH2:56][CH2:55][N:54]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)[CH2:53][CH2:52]1)=[O:4]

Participants

3

Reactant 1

HCID 15222072HCID 15222072, compound

Product 1

HCID 178440121HCID 178440121, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methoxycarbonyl-4-[4-(2-pyridyl)-piperazin-1-yl]methyl-2-propyl-1-[(2'-(N-trityltetrazol-5-yl)biphen-4-yl)methyl]imidazole (1.72 g, 2.10 mmol), obtained from Part B of Example 101, was stirred in 75 mL methanol at reflux for 2 hours. After evaporation of solvent under reduced pressure, the residue was stirred in 30 mL of 1:1 methanol/5% aqueous NaHCO3 for 6 h. The reaction mixture was extracted with 4×50 mL ethyl ether, and the residual organic solvent in the aqueous layer was evaporated under reduced pressure. The product was precipitated by adjusting the pH to 5 with aqueous HCl. The title compound (1.02 g, 84.2%) was collected as a white powder after filtering and drying in vacuo at 60° C. 1H NMR (300 MHz, CDCl3): δ 0.86 (t, J=7.3 Hz, 3H); 1.61 (m, 2H); 2.54 (t, J=7.7 Hz, 2H); 2.76 (br s, 4H, piperazine); 3.54 (br s, 4H, piperazine); 3.63 (s, 3H); 3.88 (s, 2H); 5.27 (s, 2H); 6.57-8.13 (m, 12H).

Workup

  1. temperatureat reflux for 2 hours
  2. customAfter evaporation of solvent under reduced pressure
  3. extractionThe reaction mixture was extracted with 4×50 mL ethyl ether
  4. customthe residual organic solvent in the aqueous layer was evaporated under reduced pressure
  5. customThe product was precipitated
  6. customThe title compound (1.02 g, 84.2%) was collected as a white powder
  7. filtrationafter filtering
  8. customdrying in vacuo at 60° C

Sources & evidence

ORD record
ord-024c6c019eea40f6b9a5d1d3dd6b797f
Source dataset
uspto-grants-1995_02
Patent number
US05389635

Reaction notes

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