Dimethylamine → HCID 19600065, 화합물

HRID 611303노트

반응식

HRID 611303 반응식
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[C:11]1([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=[O:17])[S:15][CH:14]=[CH:13][CH:12]=1.[CH2:27]([N:29]([CH2:32]C)[CH2:30]C)C.C(P(=O)(OCC)OCC)#N.CNC.C=O>ClCCl>[CH3:27][N:29]([CH2:32][C:3]1[O:2][C:10]2[CH2:9][CH2:8][N:7]([C:22](=[O:23])[C:21]3[CH:25]=[CH:26][C:18]([C:16](=[O:17])[C:11]4[S:15][CH:14]=[CH:13][CH:12]=4)=[CH:19][CH:20]=3)[CH2:6][C:5]=2[CH:4]=1)[CH3:30]

참가 물질

8

반응물 6

HCID 674DimethylamineHCID 712FormaldehydeHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochlorideHCID 196000994-(2-Thenoyl)benzoic acid

생성물 1

HCID 19600065HCID 19600065, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.279 g (1.2 mmol) of 4-(2-thenoyl)benzoic acid and 0.55 ml (4.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.24 g (1.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. After the solvent was distilled off, 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; 0.135 ml (1.50 mmol) of 50% aqueous dimethylamine and 0.122 ml (1.50 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 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). The resulting purified product was recrystallized from ethyl acetate-hexane to yield the desired product.

후처리

  1. temperaturecooling
  2. distillationAfter the solvent was distilled off
  3. additionwater was added
  4. extractionfollowed by 2 extractions with ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe resulting crude product was dissolved in 10 ml of acetic acid
  9. stirringby stirring at 100° C. for 30 minutes
  10. distillationAfter the solvent was distilled off under reduced pressure
  11. extractionextracted with ethyl acetate 2 times
  12. washThe combined organic layer was washed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe solvent was distilled off under reduced pressure
  15. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)
  16. customThe resulting purified product
  17. customwas recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-5a04089fa709499d837ff6d5ac5a6a23
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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