HCID 19008932, compound → HCID 178441753, compound

HRID 1742414Notes

Reaction equation

HRID 1742414 reaction equation
[CH2:1]([C:5]1[N:6]([CH:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]4[N:32](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:31]=[N:30][N:29]=4)=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[C:7]([Cl:12])=[C:8]([CH2:10][OH:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]>CO>[CH2:1]([C:5]1[N:6]([CH:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]4[NH:32][N:31]=[N:30][N:29]=4)=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[C:7]([Cl:12])=[C:8]([CH2:10][OH:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 19008932HCID 19008932, compound

Product 1

HCID 178441753HCID 178441753, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2-butyl-5-chloro-1-{5-[2-(1-trityl-1H-tetrazol-5-yl)-phenyl]-indan-1-yl}-1H-imidazol-4-yl)-methanol (100 mg) in MeOH (10 mL) was heated under reflux for 8 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was chromatographed on SiO2 -gel using a gradient of 2% MeOH/CH2Cl2 to 15% MeOH/CH2Cl2 to give 31 mg of a colorless oil. The oil was dissolved in EtOAc (0.5 mL) and hexanes were added to precipitate a solid. The solid was filtered and dried. 1H NMR (250 MHz, d6 -DMSO): d 7.67 (d, 1 H), 7.40 (m, 4 H), 7.05 (s, 1 H), 6.90 (d, 1 H), 6.60 (d, 1 H), 5.95 (t, 1 H), 5.85 (bs, 1 H), 4.18 (s, 2 H), 3.50-2.30 (m), 1.54 (m, 2 H), 1.46 (m, 2 H), 0.90 (t, 2 H).

Workup

  1. temperatureunder reflux for 8 hours
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record
ord-3d3c217350f14d4e9a43504ec5fd7c0f
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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