Imidazole → HCID 20030823, compound

HRID 232035Notes

Reaction equation

HRID 232035 reaction equation
[C:1]([O:4][CH2:5][C:6](Cl)=[O:7])(=[O:3])[CH3:2].N1C=CN=C1.[NH2:14][C:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:1]([O:4][CH2:5][C:6]([NH:21][C:20]1[C:15]([NH2:14])=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 99562,3-DiaminopyridineHCID 26297Acetoxyacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 20030823HCID 20030823, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Acetoxyacetyl chloride (2.73 g, 20 mmol) was added dropwise to a stirred solution of imidazole (2.72 g, 40 mmol) in dry tetrahydrofuran (20 ml) under nitrogen at 0° C. After the addition was complete, the thick white suspension was cooled to --78° C. and a solution of 2,3-diaminopyridine (2.18 g, 20 mmol) in dry tetrahydrofuran (60 ml) was added over 10 minutes. The mixture was allowed to warm to room temperature overnight and then saturated aqueous sodium bicarbonate (100 ml) was added. The mixture was extracted with dichloromethane (3×80 ml), the extracts were dried (MgSO4) and concentrated under reduced pressure to give a brown solid. Recrystallisation from ethyl acetate gave 3-(acetoxyacetyl)amino-2-aminopyridine (795 mg, 38%) as white flakes.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature overnight
  3. extractionThe mixture was extracted with dichloromethane (3×80 ml)
  4. dry with materialthe extracts were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown solid
  7. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-86cfdd6da5534ca4b2a723b150318aec
Source dataset
uspto-grants-1989_07
Patent number
US04851412

Reaction notes

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