Dimethylamine → HCID 19599922, compound

HRID 611386Notes

Reaction equation

HRID 611386 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[C:11]1([C:17]2([C:22]3[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=3)[S:21][CH2:20][CH2:19][S:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:31]([N:33]([CH2:36]C)[CH2:34]C)C.C(P(=O)(OCC)OCC)#N.CNC.C=O>CN(C)C=O.O>[CH3:31][N:33]([CH2:36][C:3]1[O:2][C:6]2[CH2:7][N:8]([C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([C:17]4([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[S:21][CH2:20][CH2:19][S:18]4)=[CH:23][CH:24]=3)[CH2:9][CH2:10][C:5]=2[CH:4]=1)[CH3:34]

Participants

9

Reactant 6

HCID 674DimethylamineHCID 712FormaldehydeHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 22262276HCID 22262276, compound

Product 1

HCID 19599922HCID 19599922, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.319 g (2.000 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.665 g (2.2 mmol) of 4-(2-phenyl-1,3-dithiolan-2-yl)benzoic acid and 1.1 ml (8.0 mmol) of triethylamine in 30 ml of N,N-dimethylformamide, 0.489 g (3.0 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. Water was added, followed by 2 extractions with ethyl acetate. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was dissolved in 10 ml of acetic acid; 0.270 ml (3.00 mmol) of 50% aqueous dimethylamine and 0.245 ml (3.00 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate, and extracted with ethyl acetate 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. extractionfollowed by 2 extractions with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe resulting crude product was dissolved in 10 ml of acetic acid
  7. stirringby stirring at 100° C. for 60 minutes
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. extractionextracted with ethyl acetate 2 times
  10. washThe combined organic layer was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)

Sources & evidence

ORD record
ord-cbb5669e8f534a71af933879c08e6118
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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