Dipropylamine → HCID 14390448, compound

HRID 1709602Notes

Reaction equation

HRID 1709602 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([OH:21])=O)[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:34]([NH:37][CH2:38][CH2:39][CH3:40])[CH2:35][CH3:36]>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:18][C:19]([N:37]([CH2:38][CH2:39][CH3:40])[CH2:34][CH2:35][CH3:36])=[O:21])[C:9]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390445HCID 14390445, compound

Product 1

HCID 14390448HCID 14390448, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 5-chloro-2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.1 g, 0.00963 mole) and 1,1'-carbonyldiimidazole (1.56 g, 0.00963 mole) in tetrahydrofuran (100 ml) was refluxed for 3.25 hours under nitrogen, cooled to room temperature, a stream of nitrogen was bubbled through the solution for 0.75 hr then a solution of dipropylamine (2.92 g, 0.0289 mole) in tetrahydrofuran (4 ml) was added. The reaction mixture was refluxed overnight under nitrogen and evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate, the layers were separated, sodium chloride was added to the aqueous layer and it was re-extracted with ethyl acetate. The combined organic layers were washed twice with a saturated sodium chloride solution, dried over magnesium sulfate, charcoaled, filtered and evaporated under reduced pressure to a solid (3.7 g, 95% yield). The solid was recrystallized from isopropyl alcohol/water and dried under high vacuum at 58° C. to give 2.11 g of title compound, mp 170°-173.5° C.

Workup

  1. temperaturewas refluxed for 3.25 hours under nitrogen
  2. customa stream of nitrogen was bubbled through the solution for 0.75 hr
  3. temperatureThe reaction mixture was refluxed overnight under nitrogen
  4. customevaporated under reduced pressure
  5. customThe residue was partitioned between water and ethyl acetate
  6. customthe layers were separated
  7. additionsodium chloride was added to the aqueous layer and it
  8. extractionwas re-extracted with ethyl acetate
  9. washThe combined organic layers were washed twice with a saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered

Sources & evidence

ORD record
ord-67ac45f2ccc34e81be0c4bda62d19de9
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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