Diethylamine → HCID 14390316, compound

HRID 2351704Notes

Reaction equation

HRID 2351704 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([CH2:18][C:19](O)=[O:20])[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37]>O1CCCC1>[CH2:36]([N:38]([CH2:39][CH3:40])[C:19](=[O:20])[CH2:18][N:17]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[N:10]=[C:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:22])([F:23])[F:1])=[CH:8][CH:7]=1)[CH3:37]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 682631,1'-Carbonyldiimidazole2×HCID 15617192HCID 15617192, compound

Product 1

HCID 14390316HCID 14390316, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-trifluoromethylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (10.0 g, 0.0312 mole), 1,1'-carbonyldiimidazole (6.1 g, 0.0374 mole), and dry tetrahydrofuran (250 ml) was stirred at room temperature for 3 hr with a stream of nitrogen bubbling through it. An additional 6.1 g (0.0374 mole) of 1,1'-carbonyldiimidazole was added, and the suspension was stirred at room temperature under nitrogen overnight. The suspension was heated at 50° C. for 2 hours and then treated with diethylamine (7.07 g, 0.097 mole) in dry tetrahydrofuran (10 ml). The reaction mixture was heated at 50° C. for 5 hr and allowed to stand at room temperature over the weekend. The solvent was evaporated under reduced pressure, the resulting solid was triturated in water (200 ml) and filtered. The solid was dissolved in hot isopropyl alcohol, treated with charcoal and filtered while hot. Upon cooling, a solid precipitated. The solid was filtered and rinsed with isopropyl ether to give 6.4 g (55%) of white solid, mp. 140.5°-142.5° C.

Workup

  1. stirringthe suspension was stirred at room temperature under nitrogen overnight
  2. temperatureThe suspension was heated at 50° C. for 2 hours
  3. temperatureThe reaction mixture was heated at 50° C. for 5 hr
  4. customto stand at room temperature over the weekend
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting solid was triturated in water (200 ml)
  7. filtrationfiltered
  8. dissolutionThe solid was dissolved in hot isopropyl alcohol
  9. additiontreated with charcoal
  10. filtrationfiltered while hot
  11. temperatureUpon cooling
  12. customa solid precipitated
  13. filtrationThe solid was filtered
  14. washrinsed with isopropyl ether

Sources & evidence

ORD record
ord-4a8770424cc64a9bb2df673238d6d11e
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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