1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 14390471, compound

HRID 622986Notes

Reaction equation

HRID 622986 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:29]([CH2:30]C(O)=O)[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[N:22]=1>C1C=CC=CC=1>[CH3:14][C:11]([O:10][C:6](=[O:5])[CH2:30][N:29]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[N:22]=[C:21]1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=1)([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 15617180HCID 15617180, compound

Product 1

HCID 14390471HCID 14390471, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Under a nitrogen atmosphere, N,N-dimethylformamide-di-tert-butyl acetal (8.12 g, 0.040 mole) was added dropwise over a 20-minute period to a stirred, refluxing suspension of 2-(2-pyridyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (2.54 g, 0.010 mole) in anhydrous benzene (50 ml). The resulting solution was refluxed for 1 hour and allowed to cool to room temperature. The reaction mixture was washed with 10% potassium carbonate solution (2×25 ml), water (25 ml), dried over sodium sulfate and concentrated in vacuo. The residue (3.5 g) was dissolved in tetrahydrofuran and treated with excess ethereal hydrogen chloride. The crystalline solid was recrystallized from tetrahydrofuran, giving 1.5 g (43%). Drying in vacuo at 65° C. for 8 hours and then at 78° C. overnight gave 1.4 g of the compound as the free base, mp 124°-125.5° C.

Workup

  1. temperaturerefluxing
  2. temperatureThe resulting solution was refluxed for 1 hour
  3. washThe reaction mixture was washed with 10% potassium carbonate solution (2×25 ml), water (25 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue (3.5 g) was dissolved in tetrahydrofuran
  7. additiontreated with excess ethereal hydrogen chloride
  8. customThe crystalline solid was recrystallized from tetrahydrofuran
  9. customgiving 1.5 g (43%)
  10. customDrying in vacuo at 65° C. for 8 hours

Sources & evidence

ORD record
ord-a2b777618af648749d8dd7045238f0f3
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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