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

HRID 2351650Notes

Reaction equation

HRID 2351650 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-ditert-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-171c3beb4f5a4c818711972ac503fd07
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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