Methyl 6-(cyclohexylamino)-5-nitronicotinate → Methyl 3-cyclohexyl-2-(4-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine-6-carboxylate

HRID 392981Notes

Reaction equation

HRID 392981 reaction equation
[CH:1]1([NH:7][C:8]2[C:17]([N+:18]([O-])=O)=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[OH:22][C:23]1[CH:33]=[CH:32][C:26]([C:27](=N)OCC)=[CH:25][CH:24]=1>CO>[CH:1]1([N:7]2[C:8]3=[N:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:16]=[C:17]3[N:18]=[C:27]2[C:26]2[CH:32]=[CH:33][C:23]([OH:22])=[CH:24][CH:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 22660792Methyl 6-(cyclohexylamino)-5-nitronicotinateHCID 135442973Ethyl 4-hydroxybenzimidate hydrochloride

Product 1

HCID 135674093Methyl 3-cyclohexyl-2-(4-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine-6-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of intermediate 58 (5.0 g, 20.0 mmol) and ethyl 4-hydroxybenzimidate hydrochloride (6.0 g, 30.0 mmol) in methanol (67 mL) was heated at reflux for 22 h. The reaction mixture was then cooled to rt and the precipitated solid was collected by vacuum filtration and washed sparingly with cold methanol to afford intermediate 59 as a white solid (6.13 g, 88%). ESI-MS m/e 352.2 (M+1).

Workup

  1. temperatureat reflux for 22 h
  2. filtrationthe precipitated solid was collected by vacuum filtration
  3. washwashed sparingly with cold methanol

Sources & evidence

ORD record
ord-fb0db238a1b8436e86c5242a3d404d20
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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