Triethylamine → HCID 14390244, compound

HRID 2072985Notes

Reaction equation

HRID 2072985 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH2:34]([O:36][C:37](=[O:42])[CH2:38][CH2:39][CH2:40][NH2:41])[CH3:35].C(N(CC)CC)C>O1CCCC1>[CH2:34]([O:36][C:37](=[O:42])[CH2:38][CH2:39][CH2:40][NH:41][C:18](=[O:20])[CH2:17][N:16]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 126496614-Aminobutyrate ethyl hydrochlorideHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390244HCID 14390244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole) and 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 3 hrs. Then, under nitrogen atmosphere, 4-aminobutyric acid ethyl ester hydrochloride (3.19 g, 0.019 mole) and triethylamine (1.92 g, 0.019 mole) were added simultaneously and the reaction mixture was allowed to stir at room temperature overnight. The tetrahydrofuran was evaporated to dryness and the residue was partitioned between methylene chloride and water. The combined methylene chloride layers were extracted with dilute sodium hydroxide, then with water. The methylene chloride layer was separated, dried, and evaporated to dryness (5.3 g) (76% crude yield). A 2-g sample was recrystallized from absolute ethanol, and dried under high vacuum overnight to give 1.47 g, mp. 169°-71° C.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe tetrahydrofuran was evaporated to dryness
  3. customthe residue was partitioned between methylene chloride and water
  4. extractionThe combined methylene chloride layers were extracted with dilute sodium hydroxide
  5. customThe methylene chloride layer was separated
  6. customdried
  7. customevaporated to dryness (5.3 g) (76% crude yield)
  8. customA 2-g sample was recrystallized from absolute ethanol
  9. customdried under high vacuum overnight
  10. customto give 1.47 g, mp. 169°-71° C.

Sources & evidence

ORD record
ord-dd998da57cb8457ea6ad94100113c71f
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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