Dipropylamine → HCID 14390411, compound

HRID 2351759Notes

Reaction equation

HRID 2351759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@H:17]([CH3:21])[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.[CH2:34]([NH:37][CH2:38][CH2:39][CH3:40])[CH2:35][CH3:36]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([C@H:17]([CH3:21])[C:18]([N:37]([CH2:38][CH2:39][CH3:40])[CH2:34][CH2:35][CH3:36])=[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 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390428HCID 14390428, compound

Product 1

HCID 14390411HCID 14390411, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (R)-2-(4Chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0166 mole). 1,1'-carbonyldiimidazole (2.69 g, 0.0166 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 2.25 hours with nitrogen bubbling through it. A solution of dipropylamine (5.04 g, 0.050 mole) in tetrahydrofuran (7 ml) was added and the reaction mixture was refluxed under nitrogen for two days. The solvents were removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was washed twice with water, twice with a 5% potassium hydroxide solution, and twice again with water. It was then dried over magnesium sulfate, charcoaled, filtered, and evaporated to an oil which crystallized upon trituration with isopropyl ether. The solid was collected by filtration and dried under high vacuum at 50° C. overnight to give 1.96 g (31%) of title compound, mp 95°-97° C.

Workup

  1. temperaturethe reaction mixture was refluxed under nitrogen for two days
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe ethyl acetate layer was washed twice with water, twice with a 5% potassium hydroxide solution
  5. dry with materialIt was then dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to an oil which
  8. customcrystallized upon trituration with isopropyl ether
  9. filtrationThe solid was collected by filtration
  10. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-bb83255d06ee47139b575c84cd4c0ef6
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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