N,N-Dimethylethylenediamine → HCID 14390292, compound

HRID 2351687Notes

Reaction equation

HRID 2351687 reaction equation
[Br: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:21](N1C=CN=C1)([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)=O.CN(C)CCN>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:25][CH2:26][CH2:27][N:23]([CH3:24])[CH3:21])=[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 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390292HCID 14390292, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0151 mole), 1,1'-carbonyldiimidazole (2.45 g, 0.0151 mole), and anhydrous tetrahydrofuran (100 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 3 hours. The nitrogen flow was stopped and a solution of N,N-dimethylethylenediamine (1.46 g, 0.0166 mole) in dry tetrahydrofuran (25 ml) was added. The solution was stirred at room temperature under nitrogen for 2 hours. The reaction mixture was concentrated in vacuo and the residue triturated in water (100 ml) and filtered. The filter cake was recrystallized from ethanol-isopropyl ether-tetrahydrofuran to give 4.45 g (73%) of white flakes, mp 195°-197° C.

Workup

  1. stirringThe solution was stirred at room temperature under nitrogen for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue triturated in water (100 ml)
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from ethanol-isopropyl ether-tetrahydrofuran
  6. customto give 4.45 g (73%) of white flakes, mp 195°-197° C.

Sources & evidence

ORD record
ord-21beefb2b51a4b69b0505c8f8f1a39ec
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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