Triethylamine → HCID 19860141, compound

HRID 2072958Notes

Reaction equation

HRID 2072958 reaction equation
ClC([O:4][CH2:5][CH3:6])=O.[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2(CC(O)=O)[NH:22][C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[NH:15]2)[CH:9]=1.C(N(CC)CC)C.[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[N:22]([CH2:6][C:5]([CH:39]3[CH2:40][N:35]([CH3:34])[CH2:36][CH2:37][NH:38]3)=[O:4])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 531671-MethylpiperazineHCID 86742454HCID 86742454, compound

Product 1

HCID 19860141HCID 19860141, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of ethyl chloroformate (0.66 g, 0.0061 mole) in 20 ml of methylene chloride was added slowly to a solution of 2-(4-chloro-2-pyridinyl)-3H-imidazo[4,5-b]pyridine acetic acid (1.75 g, 0.006 mole) and triethylamine (0.68 g, 0.0067 mole) in 75 ml of methylene chloride. After the solution was allowed to stir at room temperature for 2 hrs, a solution of N-methylpiperazine (0.61 g, 0.0061 mole) in methylene chloride was added slowly at room temperature and allowed to stir overnight. The reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was partitioned between dilute hydrochloric acid and diethyl ether. The aqueous layer was separated and extracted with diethyl ester (2×) and methylene chloride (3×). The aqueous layer was neutralized (pH 7) and refrigerated. The small amount of precipitate was removed by filtration. The aqueous filtrate was basified and extracted with methylene chloride (3×). The methylene chloride extracts were combined and evaporated to a gum. The gummy residue was purified by alumina column chromatography (Brockman activity 1, 80-200 mesh, 40 g) by elution with 20% acetone/80% benzene. The appropriate fractions (TLC) were combined and evaporated. The residue was crystallized from acetone/petroleum ether (bp 50°-110° C.). The crystalline solid was collected, washed with petroleum ether and isopropyl ether, and dried under high vacuum at room temperature to give 0.54 g (24%) of title compound, mp 174°-75° C.

Workup

  1. stirringto stir overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was partitioned between dilute hydrochloric acid and diethyl ether
  5. customThe aqueous layer was separated
  6. extractionextracted with diethyl ester (2×) and methylene chloride (3×)
  7. customThe small amount of precipitate was removed by filtration
  8. extractionextracted with methylene chloride (3×)
  9. customevaporated to a gum
  10. customThe gummy residue was purified by alumina column chromatography (Brockman activity 1, 80-200 mesh, 40 g) by elution with 20% acetone/80% benzene
  11. customevaporated
  12. customThe residue was crystallized from acetone/petroleum ether (bp 50°-110° C.)
  13. customThe crystalline solid was collected
  14. washwashed with petroleum ether and isopropyl ether
  15. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-8ff33803886549b4bccaca0d35e3fc7c
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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