Tetrahydrofuran → 2-(3-Chlorophenyl)-3-[2-(4-methyl-1-piperazinyl)-2-oxoethyl]3H-imidazo[4,5-b]pyridine fumarate

HRID 621887Notes

Reaction equation

HRID 621887 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=[O:22].[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[O:40]1[CH2:44][CH2:43]CC1>>[C:44]([OH:40])(=[O:22])/[CH:43]=[CH:17]/[C:18]([OH:20])=[O:19].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([N:37]3[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]3)=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 531671-MethylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 230373162-(3-Chlorophenyl)-3-[2-(4-methyl-1-piperazinyl)-2-oxoethyl]3H-imidazo[4,5-b]pyridine fumarateYield 46%

Procedure

A stream of nitrogen gas was bubbled through a stirred solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.68 g, 0.0128 mole), 1,1'-carbonyldiimidazole (2.07 g, 0.0128 mole), and anhydrous tetrahydrofuran (70 ml) for 21/2 hrs. at room temperature. A solution of N-methylpiperazine in 10 ml of tetrahydrofuran was added (rapid drop) and stirring was continued for 4 hrs. at room temperature. The tetrahydrofuran was evaporated and the residue was dissolved in methylene chloride (75 ml). The methylene chloride solution was washed with water (2×30 ml), dried over sodium sulfate, and concentrated in vacuo. The residue was converted to the sesquifumarate salt and crystallized from isopropyl alcohol-isopropyl ether. Recrystallization twice from isopropyl alcohol-isopropyl ether gave 3.2 g (46%) of a white solid, mp 190°-193° C. with decomposition.

Workup

  1. customat room temperature
  2. customat room temperature
  3. customThe tetrahydrofuran was evaporated
  4. dissolutionthe residue was dissolved in methylene chloride (75 ml)
  5. washThe methylene chloride solution was washed with water (2×30 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customcrystallized from isopropyl alcohol-isopropyl ether
  9. customRecrystallization twice from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-dbf30372237f4a8195628c45d2ebf503
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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