Glycine ethyl ester → N-[[2(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridin-3-yl]acetyl]glycine ethyl ester

HRID 621914Notes

Reaction equation

HRID 621914 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([O:35][C:36](=[O:39])[CH2:37][NH2:38])[CH3:34]>O1CCCC1>[CH2:33]([O:35][C:36](=[O:39])[CH2:37][NH:38][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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:34]

Participants

5

Reactant 3

HCID 12176Glycine ethyl esterHCID 682631,1'-CarbonyldiimidazoleHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390237N-[[2(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridin-3-yl]acetyl]glycine ethyl esterYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (9.50 g, 0.033 mole), 1,1'-carbonyldiimidazole (5.35 g, 0.033 mole) and anhydrous tetrahydrofuran (300 ml) was stirred at room temperature for 2 hrs with a stream of nitrogen bubbling through it. To the resulting suspension was added glycine ethyl ester (8.0 g, 0.078 mole) and the solution stirred over the weekend. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate (150 ml) and potassium bicarbonate solution (75 ml). The organic layer was washed with potassium bicarbonate solution (2×50 ml), water (50 ml), brine (25 ml), dried over sodium sulfate, and concentrated in vacuo. The residue (10 g) was recrystallized from tetrahydrofuran-isopropyl ether to give 6.93 g (56%) of an off-white solid, m.p. 144°-145° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (150 ml) and potassium bicarbonate solution (75 ml)
  4. washThe organic layer was washed with potassium bicarbonate solution (2×50 ml), water (50 ml), brine (25 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue (10 g) was recrystallized from tetrahydrofuran-isopropyl ether

Sources & evidence

ORD record
ord-e04e73172fbf4c0983c5ea809538612e
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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