Diethylamine → HCID 14390333, compound

HRID 621973Notes

Reaction equation

HRID 621973 reaction equation
[CH3:1][O:2][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.[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35]>O1CCCC1>[OH2:2].[CH2:34]([N:36]([CH2:37][CH3:38])[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]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH3:35]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 15617195HCID 15617195, compound

Product 1

HCID 14390333HCID 14390333, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen bubbling, a mixture of 2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.2 g, 0.015 mole) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 3 hrs. The diethylamine (2.19 g, 0.03 mole) was added and the reaction mixture was allowed to stir at room temperature overnight, then heated at reflux for 3 hrs. The tetrahydrofuran was evaporated to dryness. The residue was treated with hot water, filtered through a Celite pad, and allowed to crystallize upon cooling. The solid was collected by filtration, washed with water, and dried under high vacuum at 50°-60° C. overnight to give 1.0 g, mp (softens at 55° C., resolidified) 133°-35° C. Total yield in 2 crops was 1.9 g (38%).

Workup

  1. stirringto stir at room temperature overnight
  2. temperatureheated
  3. temperatureat reflux for 3 hrs
  4. customThe tetrahydrofuran was evaporated to dryness
  5. additionThe residue was treated with hot water
  6. filtrationfiltered through a Celite pad
  7. customto crystallize
  8. temperatureupon cooling
  9. filtrationThe solid was collected by filtration
  10. washwashed with water
  11. customdried under high vacuum at 50°-60° C. overnight
  12. customto give 1.0 g, mp (softens at 55° C., resolidified) 133°-35° C
  13. customTotal yield in 2 crops

Sources & evidence

ORD record
ord-0ef99b7db7d64896b115c3ae471f1bed
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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