m-Chloroperbenzoic acid → HCID 178439932, compound

HRID 1729448Notes

Reaction equation

HRID 1729448 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12.ClC1C=C(C=CC=1)C(OO)=[O:37]>>[CH3:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:37])=[C:4]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178439909HCID 178439909, compound

Product 1

HCID 178439932HCID 178439932, compoundYield 42.8%

Procedure

A solution of 7-Methyl-2-propyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine (9 mg) and m-chloroperoxybenzoic acid (6 mg) CHCl3 (2 mL) was heated to reflux for 2 hours. Concentration and purification (SiO2, 80:20:1 CH2Cl2 /MeOH/NH4OH) gave 4 mg of the title compound as a solid. 1H NMR (300 MHz, CD3OD) δ 8.07 (d, 1H, J=6 Hz), 7.60-7.43 (m, 4H), 7.19, (d, 1 H, J=6 Hz), 7.09 (s, 4H), 6.14 (s, 2H), 2.82 (t, 2H, J=7.5 Hz), 2.63 (s, 3H), 1.81-1.67 (m, 2H), 0.98 (t, 3H, J=7.5 Hz).

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationConcentration and purification (SiO2, 80:20:1 CH2Cl2 /MeOH/NH4OH)

Sources & evidence

ORD record
ord-656fa1618da247f6828301b658c92255
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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