Dimethylamine → HCID 14390222, compound

HRID 2351647Notes

Reaction equation

HRID 2351647 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]([OH:21])=O)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.[C:24](N1C=CN=C1)([N:26]1C=CN=[CH:27]1)=O.CNC>O1CCCC1>[CH3:24][N:26]([CH3:27])[C:19](=[O:21])[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

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 15617192HCID 15617192, compound

Product 1

HCID 14390222HCID 14390222, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-trifluoromethylphenyl)-3H-imidazo [4,5-b]pyridine-3-acetic acid (10 g, 0.031 mole), 1,1'-carbonyldiimidazole (6.0 g, 0.037 mole), and dry tetrahydrofuran (200 ml) was stirred at room temperature for 2 hr. with a stream of nitrogen bubbling through it. The suspension was heated at 50° C. under nitrogen for 2 hr, cooled in ice and treated with a solution of dimethylamine in tetrahydrofuran (4.22 g of dimethylamine in 40 ml of tetrahydrofuran.) The solution was stirred at room temperature overnight, more dimethylamine (0.71 mole in 30 ml of tetrahydrofuran) was added, and the reaction mixture was heated at 45° C. for 3 hr. The reaction mixture was concentrated under reduced pressure; the resulting solid was triturated in water, filtered, rinsed twice with water, twice with 5% potassium hydroxide solution and then twice again with water. The solid was dissolved in hot isopropyl alcohol, filtered hot, and cooled. Water was added and the solid filtered and dried at 80° C. under vacuum to yield 3.55 g (33%) of white solid, mp 181°-183° C.

Workup

  1. temperatureThe suspension was heated at 50° C. under nitrogen for 2 hr
  2. temperaturecooled in ice
  3. stirringwas stirred at room temperature overnight
  4. temperaturethe reaction mixture was heated at 45° C. for 3 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe resulting solid was triturated in water
  7. filtrationfiltered
  8. washrinsed twice with water, twice with 5% potassium hydroxide solution
  9. dissolutionThe solid was dissolved in hot isopropyl alcohol
  10. filtrationfiltered hot
  11. temperaturecooled
  12. additionWater was added
  13. filtrationthe solid filtered
  14. customdried at 80° C. under vacuum

Sources & evidence

ORD record
ord-3f2ca2b14f6f483cbbf41c038d777e46
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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