N,N-Diethyl-1,3-propanediamine → HCID 14390352, compound

HRID 2073053Notes

Reaction equation

HRID 2073053 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.[CH2:33]([N:35]([CH2:40][CH3:41])[CH2:36][CH2:37][CH2:38][NH2:39])[CH3:34]>O1CCCC1.C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:39][CH2:38][CH2:37][CH2:36][N:35]([CH2:40][CH3:41])[CH2:33][CH3:34])=[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

6

Reactant 3

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 682631,1'-CarbonyldiimidazoleHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390352HCID 14390352, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole), 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 2 hours with nitrogen bubbling through it. A solution of 3-diethylaminopropylamine (6.8 g, 0.0522 mole) in tetrahydrofuran (10 ml) was added and the reaction mixture was stirred at room temperature overnight under nitrogen. The reaction mixture was evaporated under reduced pressure to give a white solid. The solid was triturated with water (50 ml), filtered and rinsed twice with water, twice with a 5% potassium hydroxide solution and twice with water to yield a white solid. The solid was dissolved in hot isopropyl alcohol and filtered. Addition of water and cooling to room temperature gave a white solid which was collected by filtration and rinsed with water to give 4.33 g (61%) of a solid. A 1.0-g sample of the solid was dried at high vacuum, mp 172° -174° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight under nitrogen
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customto give a white solid
  4. customThe solid was triturated with water (50 ml)
  5. filtrationfiltered
  6. washrinsed twice with water, twice with a 5% potassium hydroxide solution and twice with water
  7. customto yield a white solid
  8. filtrationfiltered
  9. additionAddition of water
  10. temperaturecooling to room temperature
  11. customgave a white solid which
  12. filtrationwas collected by filtration
  13. washrinsed with water

Sources & evidence

ORD record
ord-207fa8fc5b254c419df47876ecefc8b9
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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