HCID 178458534, compound → HCID 178458533, compound

HRID 1644595

Reaction equation

HRID 1644595 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:29])[CH3:28])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][CH:20]=[C:21]([CH2:23][OH:24])[CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.O=[Mn]=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:29])[CH3:28])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][CH:20]=[C:21]([CH:23]=[O:24])[CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178458534HCID 178458534, compound

Product 1

HCID 178458533HCID 178458533, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of {2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridin-6-yl}methanol (1.0 g) in dichloromethane (50 ml) was added manganese peroxide (2.3 g), and the mixture was stirred at room temperature for 8 hr. The insoluble material was removed by filtration, and the filtrate was concentrated. The obtained crude crystals were washed with diethyl ether to give the title compound (0.70 g, yield 69%) as colorless crystals. melting point 170-171° C. purity 87%. M+H: 388. 1H NMR (CDCl3) δ: 1.52 (6H, d, J=6.0 Hz), 4.76-4.85 (1H, m), 5.17 (2H, s), 7.03-7.07 (1H, m), 7.11-7.16 (1H, m), 7.31-7.52 (5H, m), 8.20 (1H, d, J=3.2 Hz), 8.53 (1H, s), 8.88 (1H, d, J=1.5 Hz), 10.19 (1H, s).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe obtained crude crystals
  4. washwere washed with diethyl ether

Sources & evidence

ORD record
ord-0eb5253243204447a038b19ebd1173d0
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Linked notes

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