Tetrahydrofuran → HCID 23037403, compound

HRID 621895Notes

Reaction equation

HRID 621895 reaction equation
[Br: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].[Br: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 14390205HCID 14390205, compound

Product 1

HCID 23037403HCID 23037403, compoundYield 45%

Procedure

A suspension of 2-(3-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.00 g, 0.0090 mole), 1,1'-carbonyldiimidazole (1.46 g, 0.0090 mole) and anhydrous tetrahydrofuran (50 ml) was stirred at room temperature with a stream of nitrogen bubbling through the mixture for 3 hrs. A solution of N-methylpiperazine (0.90 g, 0.0090 mole) in 10 ml of tetrahydrofuran (dry) was added and stirring continued at room temperature overnight. The tetrahydrofuran was evaporated and the residue dissolved in methylene chloride (50 ml) and washed with water (3×25 ml), dried over sodium sulfate, and concentrated in vacuo. The residue (3.0 g) was converted to the 11/2 fumarate salt and recrystallized twice from isopropyl alcohol-isopropyl ether, giving 2.36 g (45%) of an off-white granular solid, mp 192°-194° C. with decomposition.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature overnight
  3. customThe tetrahydrofuran was evaporated
  4. dissolutionthe residue dissolved in methylene chloride (50 ml)
  5. washwashed with water (3×25 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customrecrystallized twice from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-3820668e3eb744dc9680494549df7f01
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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