Imidazo(4,5-b)pyridine → HCID 14369779, compound

HRID 1381921Notes

Reaction equation

HRID 1381921 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[N:9]=[N:8][N:7]=1.BrCC1C=CC(C(OCC)=O)=CC=1.[NH:30]1[C:38]2[C:33](=[N:34][CH:35]=[CH:36][CH:37]=2)[N:32]=[CH:31]1.N1C2C=CN=CC=2N=C1>>[CH:11]1([N:10]2[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:32]3[C:33]4=[N:34][CH:35]=[CH:36][CH:37]=[C:38]4[N:30]=[CH:31]3)=[N:7][N:8]=[N:9]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 4

HCID 67504Imidazo(4,5-b)pyridineHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 112187395-(4-Chlorobutyl)-1-cyclohexyl-1H-tetrazoleHCID 178419860HCID 178419860, compound

Product 1

HCID 14369779HCID 14369779, compound

Procedure

Utilizing the procedure described in Example 1(a) employing 5-(4-chlorobutyl)-1-cyclohexyl-1H-tetrazole in lieu of ethyl 4-bromomethylbenzoate and imidazo[4,5-b]pyridine in lieu of imidazo[4,5-c]pyridine yielded an impure mixture of isomers. The mixture was purified by column chromatography (silica gel, 5% ethanol in chloroform) to yield a less polar isomer which was recrystallized from diethyl ether-chloroform to yield 3-[4-(1-cylohexyl-1H-tetrazol-5-yl)butyl]-3H-imidazo[4,5-b]pyridine as a colorless crystalline solid, having a melting point of 94°-95° C. and the following physical characteristics:

Workup

  1. customyielded
  2. additionan impure mixture of isomers
  3. customThe mixture was purified by column chromatography (silica gel, 5% ethanol in chloroform)
  4. customto yield a less polar isomer which
  5. customwas recrystallized from diethyl ether-chloroform

Sources & evidence

ORD record
ord-6b3964bda15647ce9200d054fa44856f
Source dataset
uspto-grants-1989_02
Patent number
US04804658

Reaction notes

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