Tetrahydrofuran → HCID 23037403, compound

HRID 2072965Notes

Reaction equation

HRID 2072965 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-f2bc9fd93c02454b9d33769f9016950e
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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