N,N-Dimethylethylenediamine → (S)-2-(4-Chlorophenyl)-N-[2-(dimethylamino)ethyl]-alpha-methyl-3H-imidazo [4,5-b]pyridine-3-acetamide

HRID 2073063Notes

Reaction equation

HRID 2073063 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@@H:17]([CH3:21])[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:22](N1C=CN=C1)([N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1)=O.CN(C)CCN>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([C@@H:17]([CH3:21])[C:18]([NH:26][CH2:27][CH2:28][N:24]([CH3:25])[CH3:22])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390427(S)-2-(4-chlorophenyl)-alpha-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390415(S)-2-(4-Chlorophenyl)-N-[2-(dimethylamino)ethyl]-alpha-methyl-3H-imidazo [4,5-b]pyridine-3-acetamideYield 32.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (S)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0166 mole), 1,1'-carbonyldiimidazole (3.21 g, 0.0198 mole) in tetrahydrofuran (100 ml) was stirred at room temperature for two hours with nitrogen bubbling through it. A solution of N,N-dimethylethylenediamine (4.41 g, 0.050 mole) in tetrahydrofuran (5.5 ml) was added and the reaction mixture was stirred at room temperature under nitrogen overnight. The solvents were removed under reduced pressure and the solid was triturated in water (100 ml). The solid was collected by filtration, rinsed once with water, twice with 5% potassium hydroxide solution and twice with water. The solid was recrystallized from hot isopropyl ether to give 1.99 g (32%) of a solid. A 0.5-g sample was dried under high vacuum to give 0.49 g of title compound, mp 130°-133° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe solid was triturated in water (100 ml)
  3. filtrationThe solid was collected by filtration
  4. washrinsed once with water, twice with 5% potassium hydroxide solution and twice with water
  5. customThe solid was recrystallized from hot isopropyl ether

Sources & evidence

ORD record
ord-7d120284d88d44d6ac404944f2cc1ea2
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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